研究者データベース

研究者情報

マスター

アカウント(マスター)

  • 氏名

    石山 竜生(イシヤマ タツオ), イシヤマ タツオ

所属(マスター)

  • 工学研究院 応用化学部門 有機工業化学分野

所属(マスター)

  • 工学研究院 応用化学部門 有機工業化学分野

独自項目

syllabus

  • 2020, 有機合成化学, Advanced Organic Synthesis, 修士課程, 総合化学院, 選択性,反応機構,立体制御,分子変換反応,有機合成化学
  • 2020, 有機化学Ⅱ, Organic Chemistry II, 学士課程, 工学部, ハロゲン化アルキル、共役ジエン、芳香族化合物、アルコール、エーテル
  • 2020, 有機合成化学, Organic Synthesis, 学士課程, 工学部, 有機化学 合成化学 官能基 炭素-炭素結合生成 環形成
  • 2020, 応用化学学生実験Ⅴ, Applied Chemistry Laboratory Ⅴ, 学士課程, 工学部, 有機化学、高分子化学、安全教育、基礎実験、合成実験
  • 2020, 物質変換工学, Applied Chemistry and Biochemistry, 学士課程, 工学部, 有機合成,有機材料,化学プロセス,反応器設計,生体材料,高分子材料,分子機能,無機材料,複合材料,電子材料,光機能材料

researchmap

プロフィール情報

学位

  • 工学博士(北海道大学)

プロフィール情報

  • 石山, イシヤマ
  • 竜生, タツオ
  • ID各種

    200901030770616519

対象リソース

業績リスト

研究キーワード

  • 触媒化学   有機金属化学   有機合成化学   Chemistry of Catalysis   Organometallic Chemistry   Synthetic Organic Chemistry   

研究分野

  • ナノテク・材料 / 有機合成化学

経歴

  • 2007年04月 - 現在 北海道大学 准教授
  • 1994年 - 2007年03月 北海道大学 助教授
  • 1991年 - 1994年 北海道大学 助手
  • 1991年 - 1994年 Hokkaido University, Research Assistant
  • 1994年 - Hokkaido University, Associate Professor
  • 北海道大学大学院 准教授

学歴

  •         - 1991年   北海道大学   工学研究科   応用化学
  •         - 1991年   北海道大学
  •         - 1986年   北海道大学   工学部   応用化学
  •         - 1986年   北海道大学

受賞

  • 2002年 有機合成化学奨励賞
  • 2002年 Incentive Award in Synthetic Organic Chemistry, Japan
  • 1998年 第1回萬有奨励賞
  • 1998年 Banyu Young Chemist Award

論文

  • Ryosuke Shishido, Minami Uesugi, Rikuro Takahashi, Tsuyoshi Mita, Tatsuo Ishiyama, Koji Kubota, Hajime Ito
    Journal of the American Chemical Society 2020年07月22日 [査読有り][通常論文]
  • Hajime Ito, Ryosuke Shishido, Ikuo Sasaki, Tomohiro Seki, Tatsuo Ishiyama, Hajime Ito
    Chemistry – A European Journal 25 56 12924 - 12928 2019年10月08日 [査読有り][通常論文]
  • Hajime Ito, Yadong Pang, Tatsuo Ishiyama, Koji Kubota, Hajime Ito
    Chemistry – A European Journal 25 18 4654 - 4659 2019年03月27日 [査読有り][通常論文]
  • Yadong Pang, Tatsuo Ishiyama, Koji Kubota, Hajime Ito
    Chemistry – A European Journal 25 18 4532  Wiley 2019年03月 [査読有り][通常論文]
  • The Direct Dimesitylborylation of Benzofuran Derivatives via an Iridium-Catalyzed C–H Activation with Silyldimesitylborane
    Ryosuke Shishido, Ikuo Sasaki, Tomohiro Seki, Tatsuo Ishiyama, Hajime Ito
    Chem. Eur. J. (IF:5.16) Just Accepted 2019年 [査読有り][通常論文]
  • Hajime Ito, Tamae Seo, Tatsuo Ishiyama, Koji Kubota, Hajime Ito
    Chem. Sci. (IF:9.556) Just Accepted 10 35 8202 - 8210 2019年 [査読有り][通常論文]
  • Ikuo Sasaki, Toshiki Ikeda, Tatsunosuke Amou, Jumpei Taguchi, Hajime Ito, Tatsuo Ishiyama
    Synlett (IF:2.418) 27 10 1582 - 1586 2016年06月 [査読有り][通常論文]
     
    An iridium-catalyzed regioselective C-H borylation of pentafluoroaniline-derived heteroaromatic aldimines has been developed. Various heteroaromatic aldimines underwent borylation by bis(pinacolato)diboron to afford the corresponding borylated products in good yields in the presence of an iridium complex formed in situ from bis(cyclooctadienyl)(methoxy)iridium {[Ir(OMe)(cod)](2)} and 1,10-phenanthroline.
  • Ikuo Sasaki, Junpei Taguchi, Hana Doi, Hajime Ito, Tatsuo Ishiyama
    Chem. Asian J. (IF:3.698) 11 9 1400 - 1405 2016年05月 [査読有り][通常論文]
     
    A new process has been developed for the iridium(I)-catalyzed vinylic C-H borylation of alpha,beta-unsaturated esters with bis(pinacolato) diboron (B(2)pin(2)). These reactions proceeded in octane at temperatures in the range of 80-120 degrees C to afford the corresponding alkenylboronic compounds in high yields with excellent regio- and stereoselectivities. The presence of an aryl ester led to significant improvements in the yields of the acyclic alkenylboronates. Crossover experiments involving deuterated substrates as well as a mixture of stereoisomers confirmed that this reaction proceeds via a 1,4-addition/beta-hydride elimination mechanism. Notably, this reaction was also used to develop a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.
  • Ikuo Sasaki, Jumpei Taguchi, Shotaro Hiraki, Hajime Ito, Tatsuo Ishiyama
    CHEMISTRY-A EUROPEAN JOURNAL 21 25 9236 - 9241 2015年06月 [査読有り][通常論文]
     
    The regiodivergent CH borylation of 2,5-disubstituted heteroarenes with bis(pinacolato)diboron was achieved by using iridium catalysts formed in situ from [Ir(OMe)(cod)](2)/dtbpy (cod=1,5-cyclooctadiene, dtbpy: 4,4-di-tert-butyl-2,2-bipyridine) or [Ir(OMe)(cod)](2)/2AsPh(3). When [Ir(OMe)(cod)](2)/dtbpy was used as the catalyst, borylation at the 4-position proceeded selectively to afford 4-borylated products in high yields (dtbpy systemA). The regioselectivity changed when the [Ir(OMe)(cod)](2)/2AsPh(3) catalyst was used; 3-borylated products were obtained in high yields with high regioselectivity (AsPh3 systemB). The regioselectivity of borylation was easily controlled by changing the ligands. This reaction was used in the syntheses of two different bioactive compound analogues by using the same starting material.
  • Ikuo Sasaki, Tatsunosuke Amou, Hajime Ito, Tatsuo Ishiyama
    Org. Biomol. Chem. 12 13 2041 - 2044 2014年 [査読有り][通常論文]
     
    The development of an Ir-catalyzed ortho-C-H borylation of aromatic aldimines derived from pentafluoroaniline is reported. This reaction proceeded at 120 degrees C to afford the corresponding borylated products in high yield with good regioselectivity using an Ir complex formed in situ from [Ir(OMe)(cod)](2)/2(C6F5)(3)P in the presence of 2-norbornene.
  • Tatsuo Ishiyama, Takeaki Saiki, Emi Kishida, Ikuo Sasaki, Hajime Ito, Norio Miyaura
    Org. Biomol. Chem. 11 47 8162 - 8165 2013年12月 [査読有り][通常論文]
     
    Aromatic C-H silylation of neat arenes with 1-hydrosilatrane was found to be efficiently catalyzed by iridium catalysts composed of 1/2[Ir(OMe)(cod)]2 and 2,9-dimethyl-1,10-phenanthroline at 120 degrees C to afford the corresponding silylated products in high yields. The silylated products can be used for the Hiyama cross-coupling reaction.
  • Ikuo Sasaki, Hana Doi, Toshiya Hashimoto, Takao Kikuchi, Hajime Ito, Tatsuo Ishiyama
    CHEMICAL COMMUNICATIONS 49 68 7546 - 7548 2013年 [査読有り][通常論文]
     
    Ir(I)-catalyzed C-H borylation of 1-cycloalkenecarboxylic derivatives with bis(pinacolato)diboron affords various alkenylboronates with functional groups in excellent yields. This reaction was also used in a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.
  • Tatsuo Ishiyama, Norio Miyaura
    Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Volume 1 and 2) 1 135 - 169 2011年10月20日 [査読有り][通常論文]
  • Hiroshi Itoh, Takao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    CHEMISTRY LETTERS 40 9 1007 - 1008 2011年09月 [査読有り][通常論文]
     
    ortho-Selective C-H borylation of aryl ketones with bis(pinacolato)diboron proceeded at 120 degrees C in octane in the presence of a catalytic amount of iridium(I) complexes comprising 1/2[Ir(OMe)(cod)](2) and AsPh3.
  • Tatsuo Ishiyama, Hironori Isou, Takao Kikuchi, Norio Miyaura
    CHEMICAL COMMUNICATIONS 46 1 159 - 161 2010年 [査読有り][通常論文]
     
    Iridium complexes generated from [Ir(OMe)(COD)](2) and tris[3,5-bis(trifluoromethyl) phenyl] phosphine efficiently catalyzed the ortho-C-H borylation of benzoate esters with bis(pinacolato)diboron in octane at 80 degrees C to produce the corresponding arylboronates in high yields with excellent regioselectivities.
  • Takao Kikuchi, Jun Takagi, Tatsuo Ishiyama, Norio Miyaura
    CHEMISTRY LETTERS 37 6 664 - 665 2008年06月 [査読有り][通常論文]
     
    Vinylic C-H borylation of cyclic vinyl ethers by bis(pinacolato)diboron was effectively catalyzed by iridium complexes comprised of 1/2[Ir(OMe)(cod)](2) and 4,4'-di-tert-butyl-2,2-bipyridine in hexane or octane to give the corresponding vinylboron compounds in good yields. The reaction of 1,4-dioxene occurred even at room temperature, whereas the reactions of dihydropyran and dihydrofuran derivatives required a temperature above 80 degrees C. Although dihydropyran and dihydrofuran themselves produced regioisomeric mixtures of alpha- and beta-borylated products, similar substrates possessing substituents at the gamma-position selectively underwent borylation at the alpha-position.
  • Takao Kikuchi, Yusuke Nobuta, Junko Umeda, Yasunori Yamamoto, Tatsuo Ishiyama, Norio Miyaura
    TETRAHEDRON 64 22 4967 - 4971 2008年05月 [査読有り][通常論文]
     
    A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C-H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)](2)-(4,4'-di-tert-butyl-2,2'-bipyridine) at 25 degrees C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 degrees C in the presence of PdCl(2)(dppf) (3.0 mol %) and K(3)PO(4) in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields. (C) 2008 Elsevier Ltd. All rights reserved.
  • Takao Kikuchi, Jun Takagi, Hironori Isou, Tatsuo Ishiyama, Norio Miyaura
    CHEMISTRY-AN ASIAN JOURNAL 3 12 2082 - 2090 2008年 [査読有り][通常論文]
     
    Borylation of the vinylic C-H bond of 1,4-dioxene, 2,3-dihydrofuran, 3,4-dihydro-2H-pyran and their gamma-substituted analogs was carried out in the presence of bis(pinacolato)diboron (B(2)pin(2)) and a catalytic amount of Ir-1-dtbpy (dtbpy = 4,4'-di-tert-butyl-2,2'-bi-pyridine) complex. The two boron atoms in B(2)pin(2) participated in the coupling, thus giving two equivalents of the coupling product from one equivalent of B(2)pin(2). The borylation of 1,4-dioxene in hexane resulted in 81% yield at room temperature. The borylation of 2.3-dihydrofurans at 80 degrees C in octane suffered from low regioselectivity, and gave a mixture of alpha- and beta-coupling products even for hindered gamma-disubstutued analogs, but gamma-substituted analogs of 3,4-dihydro-2H-pyran achieved high alpha-selectivity, giving single coupling products. This protocol was applied to the syntheses of a key precursor of vineomycinone B2 methyl ester and other C-substituted D-glucals by borylation of protected D-glucals with B(2)pin(2) to give alpha-boryl glucal followed by cross-coupling with haloarenes, benzyl bromide, and allyl bromide. A catalytic cycle that involves the oxidative addition of sp(2) C-H bond to iridium(III)-trisboryl intermediate as the rate-determining step has been proposed.
  • Takeaki Saiki, Yukihiro Nishio, Tatsuo Ishiyama, Norio Miyaura
    ORGANOMETALLICS 25 26 6068 - 6073 2006年12月 [査読有り][通常論文]
     
    The aromatic C-H silylation of arenes (10 equiv) with 1,2-di-sec-butyl-1,1,2,2-tetrafluorodisilane was carried out in octane at 120 degrees C in the presence of a catalytic amount of iridium(I) complexes (3.0 mol %) generated from 1/2[Ir(OMe)(COD)](2) and 2,9-diisopropyl-1,10-phenanthroline. The reactions of many arenes resulted in the formation of corresponding arylfluorosilanes in high yields with excellent regioselectivities.
  • Tatsuo Ishiyama, Norio Miyaura
    PURE AND APPLIED CHEMISTRY 78 7 1369 - 1375 2006年07月 [査読有り][通常論文]
     
    Direct C-H borylation of aromatic compounds catalyzed by a transition-metal complex was studied as an economical protocol for the synthesis of aromatic boron derivatives. Iridium complexes generated from Ir(l) precursors and 2,2'-bipyridine ligands efficiently catalyzed the reactions of arenes and heteroarenes with bis(pinacolato)diboron or pinacolborane to produce a variety of aryl- and heteroarylboron compounds. The catalytic cycle involves the formation of a tris(boryl)iridium(III) species and its oxidative addition to an aromatic C-H bond.
  • Tatsuo Ishiyama, Norio Miyaura
    Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine 101 - 121 2006年01月31日 [査読有り][通常論文]
  • TM Boller, JM Murphy, M Hapke, T Ishiyama, N Miyaura, JF Hartwig
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 127 41 14263 - 14278 2005年10月 [査読有り][通常論文]
     
    This paper describes mechanistic studies on the functionalization of arenes with the diboron reagent B(2)pin(2) (bis-pinacolato diborane(4)) catalyzed by the combination of 4,4'-di-tert-butylbipyridine (dtbpy) and olefin-ligated iridium halide or olefin-ligated iridium alkoxide complexes. This work identifies the catalyst resting state as [Ir(dtbpy)(COE)(Bpin)(3)] (COE = cyclooctene, Bpin = 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl). [Ir(dtbpy)(COE)(Bpin)(3)] was prepared by independent synthesis in high yield from [Ir(COD)(OMe)](2), dtbpy, COE, and HBpin. This complex is formed in low yield from [lr(COD)(OMe)](2), dtbpy, COE, and B2pin2. Kinetic studies show that this complex reacts with arenas after reversible dissociation of COE. An alternative mechanism in which the arene reacts with the lr(l) complex [Ir(dtbpy)Bpin] after dissociation of COE and reductive elimination of B(2)pin(2) does not occur to a measurable extent. The reaction of [Ir(dtbpy)(COE)(Bpin)(3)] with arenes and the catalytic reaction of B(2)pin(2) with arenes catalyzed by [lr(COD)(OMe)](2) and dtbpy occur faster with electron-poor arenas than with electron-rich arenes. However, both the stoichiometric and catalytic reactions also occur faster with the electron-rich heteroarenes thiophene and furan than with arenes, perhaps because eta(2)-heteroarene complexes are more stable than the eta(2)-arene complexes and the eta(2)-heteroarene or arene complexes are intermediates that precede oxidative addition. Kinetic studies on the catalytic reaction show that [lr(dtbpy)(COE)(Bpin)(3)] enters the catalytic cycle by dissociation of COE, and a comparison of the kinetic isotope effects of the catalytic and stoichiometric reactions shows that the reactive intermediate [lr(dtbpy)(Bpin)(3)] cleaves the arene C-H bond. The barriers for ligand exchange and C-H activation allow an experimental assessment of several conclusions drawn from computational work, Most generally, our results corroborate the conclusion that C-H bond cleavage is turnover-limiting, but the experimental barrier for this bond cleavage is much lower than the calculated barrier.
  • T Ishiyama
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 63 5 440 - 452 2005年05月 [査読有り][通常論文]
     
    Direct borylation and silylation of unreactive C-H bonds catalyzed by transition metal complexes have been extensively studied by several research groups and have become economical, efficient, elegant, and environmentally benign protocols for the synthesis of a variety of organoboron and organosilicon compounds. A number of transition metal complexes catalyzes C-H borylation and silylation of alkanes, arenes, heteroarenes, alkenes, or benzylic positions of alkylarenes by diborons or hydoroboranes and disilanes or hydrosilanes to produce the corresponding alkyl-, aryl-, heteroaryl-, vinyl-, or benzylboron and -silicon compounds, respectively. In this review, seminal early works and exciting recent developments in the area of direct borylation and silylation of hydrocarbons based on C-H activation are summarized.
  • T Ishiyama, K Sato, Y Nishio, T Saiki, N Miyaura
    CHEMICAL COMMUNICATIONS 40 5065 - 5067 2005年 [査読有り][通常論文]
     
    The aromatic C-H silylation of five-membered heteroarenes with 1,2-di-tert-butyl-1,1,2,2-tetrafluorodisilane regioselectively proceeded at 120 degrees C in octane in the presence of a catalytic amount of iridium( I) complexes generated from 1/2[Ir(OMe)(COD)](2) and 2-tert-butyl-1,10-phenanthroline.
  • F Ozawa, T Ishiyama, S Yamamoto, S Kawagishi, H Murakami
    ORGANOMETALLICS 23 8 1698 - 1707 2004年04月 [査読有り][通常論文]
     
    The mechanism of C-O bond cleavage of allylic alcohols promoted by the hydridopalladium complexes PdH(OTf)(DPCB-Y) (2), bearing 1,2-diaryl-3,4-bis[(2,4,6-tri-tert-butylphenyl)-phosphinidene]cyclobutene ligands (DPCB-Y), has been investigated (aryl = 4-(trifluoro-methyl)phenyl (DPCB-CF3), phenyl (DPCB), 4-methoxyphenyl (DPCB-OMe), 4-octyloxyphenyl (DPCB-OOct)). This reaction forms the (pi-allyl)palladiuin complexes [Pd(pi-allyl)(DPCB-Y)]-OTf 1 (1), which are key intermediates for the catalytic allylation of aniline with allylic alcohols. The platinum analogue of 2 is obtained as the hydrido-bridged dimer [Pt-2(mu-H)(2)(DPCB)(2)]-(OTf)(2) (4) by the treatment of PtMe(OTf)(DPCB) (5) with HSiMe2Ph in the presence of a small amount of water. Complex 4 cleaves the C-O bond of allylic alcohols at 50 degreesC, yielding the pi-allyl complexes [Pt(pi-allyl)(DPCB)]OTf (7). Although complex 2, similarly prepared by the reaction of PdMe(OTf)(DPCB) (5) with HSiMe2Ph and water, is too unstable to be identified, its formation is confirmed by trapping experiments using dienes to give the corresponding :T-allyl complexes. Complex 2, thus generated, instantly reacts with allylic alcohols at room temperature to afford the pi-allyl complex I in high yield. The intermediacy of 2 in the catalytic allylation is further examined by kinetic experiments on actual catalytic systems, leading to mechanistic details of C-O bond cleavage promoted by 2.
  • F Ozawa, S Kawagishi, T Ishiyama, M Yoshifuji
    ORGANOMETALLICS 23 6 1325 - 1332 2004年03月 [査読有り][通常論文]
     
    Dimethylplatinum(II) complexes coordinated with 1,2-diaryl-3,4-bis[(2,4,6-tri-tert-butylphenyl)phosphinidene]cyclobutenes (DPCB-Y; aryl = 4-methoxyphenyl, phenyl, 4-trifluoromethylphenyl, 3,5-bis(trifluoromethyl)phenyl] are prepared by ligand displacement of Pt2Me4(mu-SMe2)(2) with corresponding DPCB-Y, which is a novel class of ligands having sp(2)-hybridized phosphorus as coordination atoms. Comparison of the NMR data with those of diimine- and diphosphine-coordinated analogues indicates intermediate magnitude of trans-influence of DPCB-Y ligands. This observation is supported by X-ray structural analysis. On the other hand, structural deviations of the coordinated DPCB-Y from free DPCB-Y suggest the occurrence of strong pi-back-donation from the platinum to the ligands. Reflecting the strong pi-back-donation, the ethylene protons in [PtMe(eta(2)-C2H4)(DPCB-Y)]OTf appear at delta 5.22-5.02 in the H-1 NMR spectra, the chemical shifts of which are significantly lower than those so far reported for platinum(II) complexes (ca. delta 4.0) and comparable to that of free ethylene (delta 5.30). Ethylene polymerization using methylpalladium catalysts bearing DPCB-Y ligands is also reported.
  • T Ishiyama, N Miyaura
    CHEMICAL RECORD 3 5 271 - 280 2004年 [査読有り][通常論文]
     
    Metal-catalyzed borylation of alkenes, alkynes, arenes, and organic halides with B-B or H-B compounds has been developed for the synthesis of organoboron compounds from simple organic substrates. The platinum(0)-catalyzed addition of bis(pinacolato)diboron to alkenes and alkynes provided a method for the stereoselective synthesis of cis-bis(boryl)alkanes or cis-bis(boryl)alkenes. The addition of diboron to 1,3-dienes with platinum(0) complexes provided a new access to cis- 1,4-bis(boryl)-2-butene derivatives, which are versatile reagents for diastereoselective allylboration of carbonyl compounds. The first one-step procedure for the syntheses of aryl, vinyl-, and allylboronates was achieved via crosscoupling reactions of diborons with aryl and 1-alkenyl halides or triflates and allyl acetates. Direct C-H borylation of arenes catalyzed by a transition metal complex was studied as an economical protocol for the synthesis of a variety of arylboron derivatives. Ir-catalyzed C-H borylation of arenes, heteroarenes, and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane furnished aryl, heteroaryl-, and benzylboron compounds. This article discusses the mechanisms of these reactions and their synthetic applications. (C) 2004 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 3: 271-280; 2004: Published online in Wiley InterScience (www.interscience.wiley.com) DOI 10.1002/tcr. 10068.
  • Tatsuo Ishiyama, Jun Takagi, Akihiro Kamon, Norio Miyaura
    J. Organomet. Chem. 687 2 284 - 290 2003年12月 [査読有り][通常論文]
     
    Cross-coupling reaction of bis(pinacolato)diboron with beta-(trifluoromethanes ulfonyloxy)-alpha, beta-unsaturated carbonyl compounds was carried out in the presence of PdCl(2)(PPh(3))(2)-2PPh(3) (3 mol%) and KOPh in toluene or K(2)CO(3) in dioxane for the synthesis of cyclic and acyclic beta-boryl-alpha,beta-unsaturated esters, amides, and ketones in high yields. The vinylboronates thus obtained readily participated in carbon-carbon bond formation such as cross-coupling with vinyl triflates and 1,4-addition to alpha,beta-unsaturated ketones. (C) 2003 Elsevier B.V. All rights reserved.
  • T Ishiyama
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 61 12 1176 - 1185 2003年12月 [査読有り][通常論文]
     
    Recent studies on the developments of the metal-catalyzed new borylation reactions by bis(pinacolato) diboron (1) are described. The 1, 4-addition of 1 to alpha,beta-unsaturated carbonyl compounds and nitriles proceeds in the presence of a catalytic amount of CuCl and KOAc in DMF. Subsequent treatment of the reaction mixture with water produces beta-boryl ketones, aldehydes, esters, and nitriles. Vinyl- and allylboron compounds are also obtained by the reactions of 1 with alkynes or allyl halides when using a stoichiometric amount of CuCl and KOAc. The aromatic C-H borylation of arenes or heteroarenes by 1 is effectively catalyzed by a combination of 1/2 [Ir(OMe)(COD)](2) and 4,4'-di-tert-butyl-2,2'-bipyridine in hexane. The high activity of the catalyst allows the formation of aryl- and heteroarylboron compounds in high yields at room temperature from equimolar equivalents of 1 and substrate. The direct borylation of alkylarenes by 1 catalyzed by Pd/C exclusively occurs via benzylic C-H activation to give benzylboron compounds.
  • T Ishiyama, J Takagi, Y Yonekawa, JF Hartwig, N Miyaura
    ADVANCED SYNTHESIS & CATALYSIS 345 9-10 1103 - 1106 2003年09月 [査読有り][通常論文]
     
    An iridium(I) complex generated from 1/2[Ir(OMe)(COD)](2) and 4,4'-di-tert-butyl-2,2'-bipyridine catalyzed the direct borylation of 2-substituted thiophenes, furans and pyrroles in stoichiometric amounts relative to bis(pinacolato)diboron in hexane at room temperature. The heteroarylboronates from regioselective C-H activation at the 5-position were formed in high yields. Similar borylations of unsubstituted heteroarenes with an equimolar amount of the diboron regioselectively provided 2,5-bis(boryl)heteroarenes.
  • T Ishiyama, N Miyaura
    JOURNAL OF ORGANOMETALLIC CHEMISTRY 680 1-2 3 - 11 2003年08月 [査読有り][通常論文]
     
    Since 1999, direct borylation of hydrocarbons catalyzed by a transition metal complex has been extensively studied by several groups and has become an economical, efficient, elegant, and environmentally benign protocol for the synthesis of a variety of organoboron compounds. Re-, Rh-, Ir- and Pd-catalyzed C-H borylation of alkanes, arenes and benzylic positions of alkylarenes by bis(pinacolato)diboron or pinacolborane provide alkyl-, aryl-, heteroaryl- and benzylboron compounds, respectively, In this review, seminal early works and exciting recent developments in the area of direct borylation of hydrocarbons via C-H activation are summarized. (C) 2003 Elsevier Science B.V. All rights reserved.
  • T Ishiyama, K Sato, Y Nishio, N Miyaura
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42 43 5346 - 5348 2003年 [査読有り][通常論文]
  • T Ishiyama, Y Nobuta, JF Hartwig, N Miyaura
    CHEMICAL COMMUNICATIONS 23 2924 - 2925 2003年 [査読有り][通常論文]
     
    Aromatic C-H borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane was catalyzed by an iridium complex generated from 1/2[Ir(OMe)(COD)](2) and 4,4'-di-tert-butyl-2,2'-bipyridine at room temperature in hexane and afforded the corresponding aryl- and heteroarylboronates in high yields with excellent regioselectivities.
  • 4,4,4’,4’,5,5,5’,5’-Octamethyl-2,2’-bi-1,3,2-dioxaborolane
    Tatsuo Ishiyama
    Electronic Encyclopedia of Reagents for Organic Synthesis 2003年 [査読有り][通常論文]
  • Jun Takagi, Akihiro Kamon, Tatsuo Ishiyama, Norio Miyaura
    Synlett 11 1880 - 1882 2002年11月 [査読有り][通常論文]
     
    Cross-coupling reaction of bis(pinacolato)diboron with beta-(trifluoromethanesulfonyloxy)-alpha,beta-unsaturated carbonyl compounds was carried out in the presence of PdCl(2)(PPh(3))(2)-2PPh(3) (3 mol%) and KOPh in toluene or K(2)CO(3) in dioxane for the synthesis of cyclic and acyclic beta-boryl-alpha,beta-unsaturated esters, amides, and ketones in high yields.
  • T Ishiyama, T Ahiko, N Miyaura
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124 42 12414 - 12415 2002年10月 [査読有り][通常論文]
  • T Ishiyama, Z Oohashi, T Ahiko, N Miyaura
    CHEMISTRY LETTERS 31 8 780 - 781 2002年08月 [査読有り][通常論文]
     
    Nucleophilic borylation of benzyl halides with bis(pinacolato)diboron in the presence of KOAc in toluene was effectively catalyzed by a palladium complex generated in situ from Pd(dba)(2) and (4-MeOC6H4)(3)P, giving the corresponding pinacol benzylboronates in high yields.
  • J Takagi, K Sato, JF Hartwig, T Ishiyama, N Miyaura
    TETRAHEDRON LETTERS 43 32 5649 - 5651 2002年08月 [査読有り][通常論文]
     
    The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80 100degreesC in the presence of a 1/2-[IrCl(COD)](2)-(4,4'-di-tert-butyl-2,2'-bipyridine)catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromaties was also achieved by using an almost equimolar amount of substrates and the diboron. (C) 2002 Elsevier Science Ltd. All rights reserved.
  • J Takagi, K Takahashi, T Ishiyama, N Miyaura
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124 27 8001 - 8006 2002年07月 [査読有り][通常論文]
     
    The synthesis of 1-alkenylboronic acid pinacol esters via a palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron (pin(2)B(2), pin = Me4C2O2) with 1-alkenyl halides or triflates was carried out in toluene at 50 degreesC in the presence of KOPh (1.5 equiv) and PdCl2(PPh3)(2)-2Ph(3)P (3 mol %). The borylation of acyclic and cyclic I-alkenyl bromides and triflates was achieved in high yields with complete retention of configuration of the double bonds. The method was applied to the one-pot synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence.
  • T Ishiyama, J Takagi, K Ishida, N Miyaura, NR Anastasi, JF Hartwig
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 124 3 390 - 391 2002年01月 [査読有り][通常論文]
  • Tatsuo Ishiyama, Jun Takagi, John F. Hartwig, Norio Miyaura
    Angew. Chem., Int. Ed. 41 16 3056 - 3058 2002年 [査読有り][通常論文]
  • T Ishiyama, K Ishida, N Miyaura
    TETRAHEDRON 57 49 9813 - 9816 2001年12月 [査読有り][通常論文]
     
    The cross-coupling reaction of bis-(pinacolato)diboron with chloroarenes to yield pinacol arylboronates was carried out in 1,4-dioxane at 80 degreesC in the presence of KOAc (1.5 equiv.) and Pd(dba)(2)/2.4PCy(3) (3-6 mol%). The catalyst was also effective to carry out analogous coupling with aryl bromides or triflates under milder conditions than those of the previous procedures catalyzed by PdCl2(dppf) in DMSO. (C) 2001 Elsevier Science Ltd. All rights reserved.
  • T Ishiyama, K Ishida, J Takagi, N Miyaura
    CHEMISTRY LETTERS 30 11 1082 - 1083 2001年11月 [査読有り][通常論文]
     
    Borylation at the benzylic C-H bond of alkylbenzenes with bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] or pinacolborane [(Me4C2O2)B-H] was carried out at 100 degreesC in the presence of a catalytic amount of 10% Pd/C. The reaction selectively afforded pinacol benzylboronates in good yields directly from various alkylbenzenes.
  • Kou Takahashi, Tatsuo Ishiyama, Norio Miyaura
    J. Organomet. Chem. 625 1 47 - 53 2001年04月 [査読有り][通常論文]
     
    The addition of bis(pinacolato)diboron [(Me2C2O2)B-B(O2C2Me4)] to alpha,beta -unsaturated carbonyl compounds giving beta -boryl carbonyl compounds and the addition to terminal alkynes yielding either 2-boryl-1-alkenes or 1-boryl-1-alkenes were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation between diboron and [Cu(CI)OAc]K generating a borylcopper species was proposed as the key step in the reactions because CuOAc similarly mediated both addition reactions to enones and alkynes in the presence of LiCl. (C) 2001 Elsevier Science B.V. All rights reserved.
  • T Ishiyama, J Hartwig
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 122 48 12043 - 12044 2000年12月 [査読有り][通常論文]
  • T Ishiyama, N Miyaura
    JOURNAL OF ORGANOMETALLIC CHEMISTRY 611 1-2 392 - 402 2000年10月 [査読有り][通常論文]
     
    The metal-catalyzed borylation of alkenes, alkynes, and organic electrophiles with B-B compounds was developed for the synthesis of organoboronic esters from simple organic substrates. The platinum(0)-catalyzed addition of bis(pinacolato)diboron to alkenes and alkynes stereoselectively yielded cis-bis(boryl)alkanes or cis-bis(boryl)alkenes. The addition of diboron to 1,3-dienes with a platinum(0) complex afforded a new access to the cis-1,4-bis(boryl)butene derivatives which are a versatile reagent for diastereoselective allylboration of carbonyl compounds. The cross-coupling reaction of diborons with aryl and vinyl halides or triflates, and allyl chlorides or acetates was found to yield aryl-, vinyl-, and allylboronates in high yields in the presence of a base and a palladium catalyst, which provides the first one-step procedure for the synthesis of organoboronic esters from organic electrophiles. The mechanisms and the synthetic applications of these reactions are discussed. (C) 2000 Elsevier Science S.A. All rights reserved.
  • K Takahashi, T Ishiyama, N Miyaura
    CHEMISTRY LETTERS 29 9 982 - 983 2000年09月 [査読有り][通常論文]
     
    The addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] to alpha,beta-unsaturated ketones, esters, nitriles, or terminal alkynes and the coupling with allyl chlorides were carried out in DMF at room temperature in the presence of CuCl and AcOK. The transmetalation from boron to copper generating a B-Cu species was proposed as the key step of the reactions.
  • K Takahashi, J Takagi, T Ishiyama, N Miyaura
    CHEMISTRY LETTERS 29 2 126 - 127 2000年02月 [査読有り][通常論文]
     
    The synthesis of 1-alkenylboronic acid pinacol esters via the palladium-catalyzed cross-coupling reaction of I-alkenyl halides or triflates with bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2 Me-4)] was carried out in toluene at 50 degrees C in the presence of potassium phenoxide (1.5 equivalents) and PdCl2(PPh3)(2). 2PPh(3) (3 mol%).
  • Tatsuo Ishiyama, Miki Murata, Taka-aki Ahiko, Norio Miyaura, Glenn C. Micalizio, William R. Roush
    Organic Syntheses 77 176 - 185 2000年 [査読有り][通常論文]
  • T Ishiyama, S Momota, N Miyaura
    SYNLETT 11 1790 - 1792 1999年11月 [査読有り][通常論文]
     
    Platinum(0)-catalyzed diboration of methylenecyclopropanes with bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] in toluene selectively provided the corresponding 2,4-bis(boryl)-1-butene and its analogs in good yields through the cleavage of the proximal bond of the cyclopropane ring.
  • T Ishiyama, H Miyaura
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 57 6 503 - 511 1999年06月 [査読有り][通常論文]
     
    Transition metal-catalyzed additions and cross-coupling reactions of the metal-metal compounds have attracted considerable attention as direct routes to prepare various organometallic compounds. Although the corresponding reactions of boron compounds had not yet been well developed, we recently reported the first platinum (0)-catalyzed addition reaction of bis(pinacolato) diboron (Id) to either terminal or internal alkynes to give cis-bis(boryl)alkenes. The addition of id to 1,3-dienes and alkenes with platinum(0) complexes afforded a new access to the cis-1,4-bis(boryl)butene and bis(boryl)alkane derivatives. The palladium (0)-catalyzed cross-coupling reactions of 1d with aryl halides or triflates, and allyl chlorides or acetates gave the corresponding aryl- and allylboronates in high yields, which provides the first one-step procedure for organoboronic eaters from organic electrophiles. Since (alkoxo)diborons are thermally stable and easily handled in air, the reagent can be useful as boron nucleophiles for cross-coupling reactions with organic halides. The mechanisms and the synthetic applications of those reactions are discussed.
  • T Ishiyama, H Kizaki, T Hayashi, A Suzuki, N Miyaura
    JOURNAL OF ORGANIC CHEMISTRY 63 14 4726 - 4731 1998年07月 [査読有り][通常論文]
     
    The carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles (ArI, ArBr, and ArOTf) to yield unsymmetrical biaryl ketones was carried out in anisole at 80 degrees C in the presence of a palladium catalyst and a base; The reaction selectively proceeded under an atmospheric pressure of carbon monoxide when PdCl2(PPh3)(2)(3 mol %)/K2CO3 (3 equiv) were used for aryl iodides and PdCl2(dppf) (3 mol %)/K2CO3 (3 equiv)/KI (3 equiv) for the bromides or the triflates. The carbonylation of arylboronic acids with benzyl halides gave aryl benzyl ketones.
  • T Ishiyama, T Kitano, N Miyaura
    TETRAHEDRON LETTERS 39 16 2357 - 2360 1998年04月 [査読有り][通常論文]
     
    Addition of bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me4)] to various allenes was carried out in excellent yields in the presence of Pt(PPh3)(4) at 80 degrees C or Pt(dbn)(2)/(c-Hex)(3)P at 50 degrees C. The addition to internal double bond was predominant for monosubstituted allenes, whereas the terminal diboration products were regioselectively obtained when a sterically bulky phosphine ligand of (c-Hex)(3)P and 1,1-disubstituted allenes were used. (C) 1998 Elsevier Science Ltd. All rights reserved.
  • T Ishiyama, Y Itoh, T Kitano, N Miyaura
    TETRAHEDRON LETTERS 38 19 3447 - 3450 1997年05月 [査読有り][通常論文]
     
    The cross-coupling reaction of (RO)(2)BB(OR)(2) (RO = methoxo and pinacolato) with aryl triflates to give arylboronates was carried out at 80 degrees C in the presence of PdCl2(dppf) (3 mol%), dppf (3 mol%) and KOAc (3 equivs) in dioxane. The reaction was available with various functional groups such as nitro, cyano, ester, and carbonyl groups. (C) 1997 Elsevier Science Ltd.
  • T Ishiyama, Y Itoh, T Kitano, N Miyaura
    TETRAHEDRON LETTERS 38 19 3447 - 3450 1997年05月 [査読有り][通常論文]
     
    The cross-coupling reaction of (RO)(2)BB(OR)(2) (RO = methoxo and pinacolato) with aryl triflates to give arylboronates was carried out at 80 degrees C in the presence of PdCl2(dppf) (3 mol%), dppf (3 mol%) and KOAc (3 equivs) in dioxane. The reaction was available with various functional groups such as nitro, cyano, ester, and carbonyl groups. (C) 1997 Elsevier Science Ltd.
  • T Ishiyama, M Yamamoto, N Miyaura
    CHEMICAL COMMUNICATIONS 7 689 - 690 1997年04月 [査読有り][通常論文]
     
    Bis(pinacolato)diboron selectively adds to terminal alkenes and cyclic alkenes having internal strain to provide bis(boryl)alkanes in 76-86% yields in the presence of a catalytic amount of Pt(dba)(2) at 50 degrees C.
  • TA Ahiko, T Ishiyama, N Miyaura
    CHEMISTRY LETTERS 26 8 811 - 812 1997年 [査読有り][通常論文]
     
    The cross-coupling reaction of bis(pinacolato)diboron with oxo-2-alkenyl acetates in toluene at 50 degrees C in the presence of Pd(dba)(2)/2 AsPh3 (3 mol%) to give allylboronates was followed by the intramolecular allylboration at 100 degrees C. The sequence provided cyclic homoallyl alcohols in high yields.
  • Synthesis of Arylboronates via Palladium-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Aryl Halides or Triflates
    Tatsuo Ishiyama, Norio Miyaura
    Current Topics in the Chemistry of Boron 92 - 95 1997年 [査読有り][通常論文]
  • T Ishiyama, M Mori, A Suzuki, N Miyaura
    JOURNAL OF ORGANOMETALLIC CHEMISTRY 525 1-2 225 - 231 1996年11月 [査読有り][通常論文]
     
    The synthesis of unsymmetrical sulfides was carried out in high yields by the palladium-catalyzed cross-coupling reaction of 9-organothio-9-borabicyclo[3.3.1]nonane (9-RS-9-BBN) with organic electrophiles, such as iodoarenes, 1-iodo-1-alkenes, allyl carbonate and propargyl carbonate, Iodoarenes and 1-iodo-1-alkenes were smoothly converted into the corresponding sulfides at 50 degrees C in the presence of PdCl2(dppf) (3 mol%) and K3PO4 (3 equiv.) in DMF. In contrast, the cross-coupling reaction of 9-RS-9-BBN with allyl or propargyl carbonates occurred in DMF without the assistance of a base. Both reactions catalyzed by Pd(dba)(2)-dppf regioselectively produced allyl and allenyl sulfides in excellent yields. The scope and limitations of the reactions, as well as the effects of varying the reaction conditions, are discussed.
  • T Ishiyama, M Yamamoto, N Miyaura
    CHEMICAL COMMUNICATIONS 17 2073 - 2074 1996年09月 [査読有り][通常論文]
     
    Bis(pinacolato)diboron 1 is selectively added to 1,3-dienes in the presence of an platinum(0) catalyst.
  • T Ishiyama, T Ahiko, N Miyaura
    TETRAHEDRON LETTERS 37 38 6889 - 6892 1996年09月 [査読有り][通常論文]
     
    The cross-coupling reaction of bis(pinacolato)diboron [(Me(4)C(2)O(2))BB(O(2)C(2)Me(4))] with allyl acetates regio- and E-stereoselectively provided the pinacol esters of allylboronic acids in high yields. The reaction was efficiently catalyzed by Pd(dba)(2) in DMSO at 50 degrees C. Copyright (C) 1996 Elsevier Science Ltd
  • T Ishiyama, N Matsuda, M Murata, F Ozawa, A Suzuki, N Miyaura
    ORGANOMETALLICS 15 2 713 - 720 1996年01月 [査読有り][通常論文]
     
    Tetrakis(methoxo)- or bis(pinacolato)diboron [(RO)(2)BB(OR)(2); (RO)(2) = (MeO)(2) (4a) and Me(4)C(2)O(2) (1)] added to both terminal and internal alkynes in the presence of a catalytic amount of Pt(PPh(3))(4) to provide stereodefined cis-bis(boryl)alkenes (3) in excellent yields. Because reagents and reaction conditions were sufficiently mild, the procedure was readily extended to various functionalized alkynes. Mechanistic study revealed that the oxidative addition of bis(pinacolato)diboron (1) to Pt(PPh(3))(4) generates cis-Pt(BO(2)C(2)Me(4))(2)(PPh(3))(2) (5), whose structure was fully characterized by multinuclear NMR spectroscopies as well as single-crystal X-ray diffraction analysis. Complex 5 exhibited high reactivity for insertion to the alkyne giving 3 in high yields, thus implying that the oxidative addition of the B-B bond to a Pt(O) complex is an initial step in the platinum(O)-catalyzed diboration of alkynes.
  • T Ishiyama, M Yamamoto, N Miyaura
    CHEMISTRY LETTERS 25 12 1117 - 1118 1996年 [査読有り][通常論文]
     
    (E)-1,2-Bis(boryl)-1-hexene, prepared by the platinum-catalyzed diboration of 1-hexyne with bis(pinacolato)diboron, regioselectively cross-coupled with aryl, 1-alkenyl, benzyl, and allyl halides in the presence of a palladium catalyst and a base to provide the corresponding pinacol esters of (E)-(1-butyl-1-alkenyl)boronic acid in good yields.
  • T ISHIYAMA, M MURATA, N MIYAURA
    JOURNAL OF ORGANIC CHEMISTRY 60 23 7508 - 7510 1995年11月 [査読有り][通常論文]
     
    The palladium-catalyzed cross-coupling reaction of the pinacol ester of diboronic acid [(Me(4)C(2)O(2))BB(O(2)C(2)Me(4)), 1] with haloarenes gave a direct procedure for arylboronic esters from aryl halides in a range of 60-98%. The reaction was catalyzed by PdCl2(dppf) (3 mol %) at 80 degrees C in the presence of KOAc (3 equiv) in DMSO and available with various functional groups such as nitro, cyano, ester, and carbonyl groups. The trans-ArPd(II)(OAc)(PPh(3))(2) intermediate was isolated and characterized to propose the catalytic cycle involving the transmetalation between the phenylpalladium(II) acetate complex and 1.
  • T ISHIYAMA, M MURATA, A SUZUKI, N MIYAURA
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS 3 295 - 296 1995年02月 [査読有り][通常論文]
     
    Under irradiation (tungsten lamp), the palladium-catalysed three-component cross-coupling reaction between iodoalkenes such as 6-iodo-1-hexene or their derivatives, carbon monoxide (1 atm) and 9-alkyl- or 9-aryl-9-BBN derivatives (9-BBN = 9-borabicyclo[3.3.1]nonane) produces unsymmetrical ketones in moderate to high yields; the oxidative addition of iodoalkenes to a palladium(0) complex proceeds via a radical process, thus allowing cyclization of the iodoalkenes to five-membered rings prior to the couplings with carbon monoxide and boron reagents.
  • T ISHIYAMA, H KIZAKI, N MIYAURA, A SUZUKI
    TETRAHEDRON LETTERS 34 47 7595 - 7598 1993年11月 [査読有り][通常論文]
     
    The cross-coupling reaction between arylboronic acids, carbon monoxide (1 atm), and aryl iodides in the presence of palladium catalyst and base provided unsymmetrical biaryl ketones in high yields. The choice of a suitable base and solvent was essential to achieve selective formation of the unsymmetrical biaryl ketone without a biaryl by-product.
  • T ISHIYAMA, N MATSUDA, N MIYAURA, A SUZUKI
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 115 23 11018 - 11019 1993年11月 [査読有り][通常論文]
  • T ISHIYAMA, K NISHIJIMA, N MIYAURA, A SUZUKI
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 115 16 7219 - 7225 1993年08月 [査読有り][通常論文]
     
    The addition of 9-(alkylthio)-9-borabicyclo[3.3.1]nonanes(9-(RS)-9-BBN) 1 to terminal alkynes was catalyzed by Pd(PPh3)4 (3 mol %) to produce 9-[(Z)-2-(alkylthio)-1-alkenyl]-9-BBN derivatives 2 in high yields. The reactions were highly regio- and stereoselective, and their conditions were sufficiently mild that a variety of functionalized alkenylboranes 2 with defined stereochemistry were readily synthesized. The boranes 2 exhibited exceptionally high reactivity on protonolysis with methanol to produce the Markovnikov adducts of thiols to 1-alkynes, 2-(alkylthio)-1-alkenes 3. The synthetic utility of the present reaction was demonstrated by the regio- and stereoselective one-pot synthesis of alkenyl sulfides 7 via the palladium-catalyzed thioboration-cross-coupling sequence.
  • T ISHIYAMA, T OHE, N MIYAURA, A SUZUKI
    TETRAHEDRON LETTERS 33 31 4465 - 4468 1992年07月 [査読有り][通常論文]
     
    The cross-coupling reaction between 9-alkyl-9-BBN derivatives, t-butylisocyanide, and haloarenes was carried out in dioxane at 50-degrees-C in the presence of K3PO4 and a catalytic amount of Pd(PPh3)4. The reaction provides alkyl aryl ketones in high yields after hydrolysis of the ketimine intermediates.
  • Tatsuo Ishiyama, Shigeru Abe, Norio Miyaura, Akira Suzuki
    Chem. Lett. 21 4 691 - 694 1992年04月 [査読有り][通常論文]
     
    9-Alkyl-9-BBN derivatives undergo the cross-coupling reaction with primary iodoalkanes to give the coupling products in fairly good yields in the presence of a catalytic amount of Pd(PPh3)4 and K3PO4.
  • Palladium(0)-catalyzed reaction of 9-alkyl-9-borabicyclo[3.3.1]nonane with 1-bromo-1-phenylthioethene : 4-(3-Cyclohexenyl)-2-phenylthio-1-butene
    Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki
    Organic Syntheses 71 89 - 96 1992年 [査読有り][通常論文]
  • T ISHIYAMA, N MIYAURA, A SUZUKI
    TETRAHEDRON LETTERS 32 47 6923 - 6926 1991年11月 [査読有り][通常論文]
     
    The synthesis of unsymmetrical ketones by means of the palladium-catalyzed carbonylative cross-coupling reaction of 9-alkyl-9-BBN derivatives with iodoalkanes under a carbon monoxide atmosphere is described.
  • Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki
    Synlett 10 687 - 688 1991年10月 [査読有り][通常論文]
     
    In the presence of Pd-catalyst [PdCl2(dppf) or Pd(PPh3)4] and K3PO4 as base, aryl and 1-alkenyl bromides (9 examples) react with 9-[R3Sn(CH2)n]-9-BBN (n = 2, 3, and 4) (2), obtained by hydroboration of omega-stannyl-1-alkenes (1) with 9-borabicyclo-[3.3.1]nonane (9-BBN), to give high yields of corresponding products coupled by cleavage of the C-B bond.
  • 石山 竜生
    Bull. Chem. Soc. Jpn. 64 6 1999 - 2001 1991年06月 [査読有り][通常論文]
     
    The synthesis of alpha,beta-unsaturated ketones by means of the palladium-catalyzed cross-coupling reaction between 9-alkyl-9-borabicyclo[3.3.1]nonanes (9-R-9-BBN) and 1-halo-1-alkenes under carbon monoxide atmosphere is described.
  • N SATOH, T ISHIYAMA, N MIYAURA, A SUZUKI
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 60 9 3471 - 3473 1987年09月 [査読有り][通常論文]
  • N MIYAURA, T ISHIYAMA, M ISHIKAWA, A SUZUKI
    TETRAHEDRON LETTERS 27 52 6369 - 6372 1986年 [査読有り][通常論文]

MISC

  • Yadong Pang, Tatsuo Ishiyama, Koji Kubota, Hajime Ito ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 258 2019年08月
  • Tamae Seo, Tatsuo Ishiyama, Koji Kubota, Hajime Ito ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 258 2019年08月
  • 伊藤 肇, 石山 竜生, 関 朋宏 Organometallic News 2015 (3) 112 -113 2015年08月06日 [査読無し][通常論文]
  • 第7回 有機合成化学協会東北・北海道支部 北海道地区「若手研究者によるパネルディスカッション」報告
    宮下正昭, 谷野圭持, 石山竜生, 小笠原正道, 河合英敏, 瀧本真徳, 原賢二 JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 63 (4) 379 -387 2005年04月 [査読無し][通常論文]
  • TM Boller, JF Hartwig, T Ishiyama, N Miyaura ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 226 U657 -U657 2003年09月 [査読無し][通常論文]

書籍等出版物

  • 使える!有機合成反応241実践ガイド「芳香族C-Hケイ素化反応」
    石山 竜生 (担当:共著)
    化学同人 2010年
  • 使える!有機合成反応241実践ガイド「芳香族C-Hホウ素化反応」
    石山 竜生 (担当:共著)
    化学同人 2010年
  • Handbook of C-H Transformations, Application in Organic Synthesis Volume 1
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    Wiley-VCH 2005年
  • Boronic Acids
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    Wiley-VCH 2005年
  • Boronic Acids
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    Wiley-VCH 2005年
  • Handbook of C-H Transformations, Application in Organic Synthesis Volume 1
    Tatsuo Ishiyama, Norio Miyaura 
    Wiley-VCH 2005年
  • Catalysts for Fine Chemical Synthesis, Volume 3, Metal Catalysed Carbon-Carbon Bond-Forming Reactions
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    John Wiley & Sons, Chichester 2004年
  • 実験化学講座 改訂5版 18巻 有機化合物の合成(VI) 金属を用いる有機合成「クロスカップリング反応」
    石山 竜生 (担当:共著)
    丸善 2004年
  • 有機合成のための触媒反応103「炭素―ホウ素結合形成」
    石山 竜生 (担当:共著)
    東京化学同人 2004年
  • Catalysts for Fine Chemical Synthesis, Volume 3, Metal Catalysed Carbon-Carbon Bond-Forming Reactions
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    John Wiley & Sons, Chichester 2004年
  • 触媒的C-H結合活性化が拓く新しい有機合成化学
    石山 竜生 (担当:単著)
    化学と工業 2003年
  • Transition Metal-Catalyzed Reactions of Organoboron Compounds
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    My Favorite Organic Synthesis 2002年
  • 触媒的シリル化反応における最近の進歩−ヒドロシランより生じるシリル金属錯体の新しい利用
    石山 竜生 (担当:単著)
    化学 2002年
  • アルキル−アルキル型クロスカップリング反応における最近の進歩
    石山 竜生 (担当:単著)
    Organo Metallic News 2002年
  • Transition Metal-Catalyzed Reactions of Organoboron Compounds
    Tatsuo Ishiyama, Norio Miyaura (担当:共著)
    My Favorite Organic Synthesis 2002年
  • 芳香族求電子試薬の触媒的アミノ化に見る配位子の工夫
    石山 竜生 (担当:単著)
    化学 1999年
  • 合成化学者のための実験有機金属化学「オレフィンのヒドロホウ素化とクロスカップリング反応」
    石山 竜生 (担当:共著)
    講談社サイエンティフィク 1992年

講演・口頭発表等

  • Iridium-Catalyzed Aromatic C-H Silylation by 1-Hydrosilatrane  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    Third International Conference on Advanced Organic Synthesis directed toward the Ultimate Efficiency and Practicability 2008年 ポスター発表
  • Iridium Catalyzed Aromatic C-H Borylation  [招待講演]
    Tatsuo Ishiyama
    1st Japan Singapore Bilateral Symposium on Catalysis 2008年 口頭発表(招待・特別)
  • Iridium-Catalyzed Borylation of Cyclic Vinyl Ethers via Vinylic C-H Activation  [通常講演]
    Takao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    Catalysis as the Basis for the Innvation in Materials Science 2008年 ポスター発表
  • Iridium-Catalyzed ortho-Borylation of Benzoate Esters by Diborons  [通常講演]
    Tatsuo Ishiyama, Hironori Isou, Takao Kikuchi, Norio Miyaura
    13th International Conference on Boron Chemistry 2008年 口頭発表(一般)
  • Iridium-Catalyzed ortho-Borylation of Benzoate Esters by Diborons  [通常講演]
    Tatsuo Ishiyama, Hironori Isou, Takao Kikuchi, Norio Miyaura
    13th International Conference on Boron Chemistry 2008年 口頭発表(一般)
  • Iridium-Catalyzed Aromatic C-H Silylation by 1-Hydrosilatrane  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    Third International Conference on Advanced Organic Synthesis directed toward the Ultimate Efficiency and Practicability 2008年 ポスター発表
  • Iridium-Catalyzed Borylation of Cyclic Vinyl Ethers via Vinylic C-H Activation  [通常講演]
    Takao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    Catalysis as the Basis for the Innvation in Materials Science 2008年 ポスター発表
  • Iridium Catalyzed Aromatic C-H Borylation  [招待講演]
    Tatsuo Ishiyama
    1st Japan Singapore Bilateral Symposium on Catalysis 2008年 口頭発表(招待・特別)
  • Iridium-Catalyzed C-H Silylation of Heteroarenes by Fluorodisilanes  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    International Conference on Asymmetric Organocatalysis 2007年 ポスター発表
  • Iridium-Catalyzed Borylation of Cyclic Vinyl Ethers via Vinylic C-H Activation  [通常講演]
    Takao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    14th IUPAC International Symposium on Organometallic Chemistry diorected towards Organic Synthesis 2007年 ポスター発表
  • Iridium-Catalyzed Borylation of Cyclic Vinyl Ethers via Vinylic C-H Activation  [通常講演]
    Takao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    14th IUPAC International Symposium on Organometallic Chemistry diorected towards Organic Synthesis 2007年 ポスター発表
  • Iridium-Catalyzed C-H Silylation of Heteroarenes by Fluorodisilanes  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    International Conference on Asymmetric Organocatalysis 2007年 ポスター発表
  • イリジウム触媒を用いるアレーンのC-Hホウ素化とケイ素化  [招待講演]
    石山 竜生
    日本化学会第87春季年会 2007年 口頭発表(招待・特別)
  • Vinylic C-H Borylation of Cyclic Vinyl Ethers with Bis(pinacolato)diboron Catalyzed by Iridium Complexes  [通常講演]
    Tatkao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    XXII International Conference on Organometallic Chemistry 2006年 ポスター発表
  • Aromatic C-H Silylation of Arenes with Fluorodisilanes Catalyzed by Iridiumu Complexes  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    1st International Conference on Cutting-Edge Organic Chemistry in Asia 2006年 ポスター発表
  • Aromatic C-H Silylation of Arenes with Fluorodisilanes Catalyzed by Iridiumu Complexes  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    1st International Conference on Cutting-Edge Organic Chemistry in Asia 2006年 ポスター発表
  • イリジウム触媒を用いたピナコールボランによる環状ビニルエーテルの脱水素―ホウ素化反応  [通常講演]
    石山 竜生
    第23回有機合成セミナー 2006年 ポスター発表
  • Vinylic C-H Borylation of Cyclic Vinyl Ethers with Bis(pinacolato)diboron Catalyzed by Iridium Complexes  [通常講演]
    Tatkao Kikuchi, Tatsuo Ishiyama, Norio Miyaura
    XXII International Conference on Organometallic Chemistry 2006年 ポスター発表
  • イリジウム触媒を用いた環状ビニルエーテル類の直接ホウ素化反応  [通常講演]
    石山 竜生
    第18回万有札幌シンポジウム 2006年 ポスター発表
  • Iridium-Catalyzed Direct Silylation of Arenes with Fluorodisilanes  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    The International Symposium on Dynamic Complexes 2005年 ポスター発表
  • Dehydrogenative Borylation of Aromatic Compounds with Pinacolborane Catalyzed by Iridium(I) Complexes at Room Temperature  [通常講演]
    Tatsuo Ishiyama, John F. Hartwig, Norio Miyaura
    12th International Conference on Boron Chemistry 2005年 ポスター発表
  • Dehydrogenative Borylation of Aromatic Compounds with Pinacolborane Catalyzed by Iridium(I) Complexes at Room Temperature  [通常講演]
    Tatsuo Ishiyama, John F. Hartwig, Norio Miyaura
    12th International Conference on Boron Chemistry 2005年 ポスター発表
  • Iridium-Catalyzed Direct Silylation of Arenes with Fluorodisilanes  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    The International Symposium on Dynamic Complexes 2005年 ポスター発表
  • イリジウム触媒を用いたフルオロジシランによる芳香族化合物の直接ホウ素化  [通常講演]
    石山 竜生
    第15回北海道大学触媒化学研究センター研究討論会 2005年 口頭発表(招待・特別)
  • Transition Metal-Catalyzed C-B Bond Forming Reactions via C-H Bond Activation  [招待講演]
    Tatsuo Ishiyama
    Symposiumu on Synthesis and Applications of Organoboronates 2004年 口頭発表(招待・特別)
  • Synthesis of Aromatic Boron Compounds via Transition Metal-Catalyzed reactions of Diborons  [招待講演]
    Tatsuo Ishiyama
    Syngenta Lecture 2004年 口頭発表(招待・特別)
  • Aromatic C-H Borylation with Pinacolborane Catalyzed by Iridium(I) Complexes at Room Temperature  [通常講演]
    Tatsuo Ishiyama, John F. Hartwig, Norio Miyaura
    Fifteenth International Conference on Organic Synthesis 2004年 ポスター発表
  • Aromatic C-H Borylation with Pinacolborane Catalyzed by Iridium(I) Complexes at Room Temperature  [通常講演]
    Tatsuo Ishiyama, John F. Hartwig, Norio Miyaura
    Fifteenth International Conference on Organic Synthesis 2004年 ポスター発表
  • Synthesis of Aromatic Boron Compounds via Transition Metal-Catalyzed reactions of Diborons  [招待講演]
    Tatsuo Ishiyama
    Syngenta Lecture 2004年 口頭発表(招待・特別)
  • Transition Metal-Catalyzed C-B Bond Forming Reactions via C-H Bond Activation  [招待講演]
    Tatsuo Ishiyama
    Symposiumu on Synthesis and Applications of Organoboronates 2004年 口頭発表(招待・特別)
  • 遷移金属触媒を用いたジボロンの反応  [招待講演]
    石山 竜生
    若手研究者のための有機化学札幌セミナー 2003年 口頭発表(招待・特別)
  • 精密有機合成を指向した新しい触媒的ホウ素化反応の開発  [通常講演]
    石山 竜生
    第20回有機合成化学夏季大学 2003年 口頭発表(招待・特別)
  • 石山 竜生
    京都大学学術講演会 2002年 口頭発表(招待・特別)
  • Iridium- and Palladium-Catalyzed Cross-Coupling reactions of Bis(pinacolato)diboron with Arenes  [通常講演]
    Tatsuo Ishiyama, Jun Takagi, Kousaku Ishida, Norio Miyaura, John F. Hartwig
    Post OMCOS-XI Symposium Thirty Years of the Cross-Coupling Reaction 2001年 ポスター発表
  • Synthesis of Vinylboronates via Cross-Coupling of Bis(pinacolato)diboron with Vinyl Triflates  [通常講演]
    Tatsuo Ishiyama, Jun Takagi, Akihiro Kamon, Norio Miyaura
    Post OMCOS-XI Symposium Thirty Years of the Cross-Coupling Reaction 2001年 ポスター発表
  • Synthesis of Vinylboronates via Cross-Coupling of Bis(pinacolato)diboron with Vinyl Triflates  [通常講演]
    Tatsuo Ishiyama, Jun Takagi, Akihiro Kamon, Norio Miyaura
    Post OMCOS-XI Symposium Thirty Years of the Cross-Coupling Reaction 2001年 ポスター発表
  • Iridium- and Palladium-Catalyzed Cross-Coupling reactions of Bis(pinacolato)diboron with Arenes  [通常講演]
    Tatsuo Ishiyama, Jun Takagi, Kousaku Ishida, Norio Miyaura, John F. Hartwig
    Post OMCOS-XI Symposium Thirty Years of the Cross-Coupling Reaction 2001年 ポスター発表
  • 石山 竜生
    日本化学会北海道支部学術講演会 2001年 口頭発表(招待・特別)
  • Synthesis of Organoboron Compounds Using Diboron Reagents  [招待講演]
    Tatsuo Ishiyama
    Merck Lecture 2000年 口頭発表(招待・特別)
  • Synthesis of Organoboron Compounds Using Diboron Reagents  [招待講演]
    Tatsuo Ishiyama
    Merck Lecture 2000年 口頭発表(招待・特別)
  • 石山 竜生
    10周年記念萬有製薬札幌シンポジウム 1998年 口頭発表(招待・特別)
  • 生理活性物質の合成を指向した新規なホウ素化反応の開発  [通常講演]
    石山 竜生
    第73回有機合成シンポジウム 1998年 口頭発表(一般)
  • Catalytic Diboration of Acetylenes with Tetrakis(alkoxo)diborons  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    XVIIth International Conference on Organometallic Chemistry 1996年 ポスター発表
  • Catalytic Diboration of Acetylenes with Tetrakis(alkoxo)diborons  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura
    XVIIth International Conference on Organometallic Chemistry 1996年 ポスター発表
  • Synthesis of Functionalized Ketones via Palladium-Catalyzed Carbonylative Cross-Coupling Reaction Using Organoboron Compounds  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki
    Eighth International Meeting on Boron Chemistry 1993年 ポスター発表
  • Palladium-Catalyzed Coupling Reaction of Organothioborates with Organic Derivatives  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki
    Seventh IUPAC Symposium on Organo-Metallic Chemistry directed towards Organic Synthesis 1993年 ポスター発表
  • 石山 竜生
    若手研究者のための有機化学札幌セミナー 1993年 口頭発表(招待・特別)
  • Palladium-Catalyzed Coupling Reaction of Organothioborates with Organic Derivatives  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki
    Seventh IUPAC Symposium on Organo-Metallic Chemistry directed towards Organic Synthesis 1993年 ポスター発表
  • Synthesis of Functionalized Ketones via Palladium-Catalyzed Carbonylative Cross-Coupling Reaction Using Organoboron Compounds  [通常講演]
    Tatsuo Ishiyama, Norio Miyaura, Akira Suzuki
    Eighth International Meeting on Boron Chemistry 1993年 ポスター発表
  • Tatsuo Ishiyama, Norio Miyauara, Akira Suzuki
    The 50th Aniversary International Symposium on Organic Synthesis 1992年 ポスター発表

所属学協会

  • 有機合成化学協会   日本化学会   The Society of Synthetic Organic Chemistry, Japan   The Chemical Society of Japan   

Works(作品等)

  • イリジウム触媒を用いたフルオロジシランによる芳香族化合物の直接ケイ素化(第15回北海道大学触媒化学研究センター研究討論会、札幌、日本)
    2004年
  • Synthesis of Aromatic Boron Compounds via Transition Metal-Catalyzed Reactions of Diborons (Syngenta Lecture, Bracknell, UK)
    2004年
  • Transition Metal-Catalyzed C–B Bond Forming Reactions via C–H Bond Activation (Symposium on Synthesis and Applications of Organoboronates, Durham, UK)
    2004年
  • Synthesis of Aromatic Boron Compounds via Transition Metal-Catalyzed Reactions of Diborons (Syngenta Lecture, Bracknell, UK)
    2004年
  • Transition Metal-Catalyzed C–B Bond Forming Reactions via C–H Bond Activation (Symposium on Synthesis and Applications of Organoboronates, Durham, UK)
    2004年
  • 遷移金属触媒を用いたジボロンの反応(若手研究者のための有機化学札幌セミナー、札幌、日本)
    2003年
  • 精密有機合成を指向した新しい触媒的ホウ素化反応の開発(第20回有機合成化学夏季大学、長野、日本)
    2003年
  • ジボロンを用いる触媒的ホウ素化反応(京都大学学術講演会、京都、日本)
    2002年
  • Iridium-Catalyzed Borylation of Arenes
    2001年
  • ジボロンを利用する求核的ホウ素化反応(日本化学会北海道支部学術講演会、札幌、日本)
    2001年
  • Iridium-Catalyzed Borylation of Arenes
    2001年
  • Synthesis of Organoboron Compounds Using Diboron Reagents (Merck Lecture, Rahway, USA)
    2000年
  • Synthesis of Organoboron Compounds Using Diboron Reagents (Merck Lecture, Rahway, USA)
    2000年
  • ジボロン反応剤を用いる有機合成(10周年記念萬有製薬札幌シンポジウム、札幌、日本)
    1998年
  • 遷移金属触媒を用いたチオボレート誘導体の反応(若手研究者のための有機化学札幌セミナー、札幌、日本)
    1993年

共同研究・競争的資金等の研究課題

  • 新規ホウ素共役系の構築を目的とする高効率的ホウ素基導入法の開発
    科学研究費補助金
    研究期間 : 2016年 -2019年 
    代表者 : 石山 竜生
  • 有機ホウ素化合物の革新的な合成法の開発
    科学研究費補助金:
    研究期間 : 2009年 -2011年 
    代表者 : 石山 竜生
  • 芳香族並びに脂肪族炭素−水素結合の活性化に基づくホウ素基およびケイ素基導入反応
    科学研究費補助金:
    研究期間 : 2005年 -2008年 
    代表者 : 石山 竜生
  • アリール型ホウ素化合物の直接合成法と新規触媒反応の開発
    科学研究費補助金:
    研究期間 : 2004年 -2005年 
    代表者 : 石山 竜生
  • 遷移金属触媒/ジボロン系によるビニル型ホウ素化合物の高効率的合成
    科学研究費補助金:
    研究期間 : 2002年 -2003年 
    代表者 : 石山 竜生
  • ライフサイエンスを指向したアリール型ホウ素化合物の革新的合成
    武田科学振興財団:
    研究期間 : 2003年 
    代表者 : 石山 竜生
  • ライフサイエンスを指向したアリール型ホウ素化合物の革新的合成
    秋山記念生命科学振興財団研究助成金:
    研究期間 : 2003年 
    代表者 : 石山 竜生
  • ジボロンによる芳香族炭化水素の直接ホウ素化反応
    伊藤科学振興会研究助成金:
    研究期間 : 2002年 
    代表者 : 石山 竜生
  • アリル型ホウ素反応剤の開発
    科学研究費補助金:
    研究期間 : 2000年 -2001年 
    代表者 : 石山 竜生
  • 共役ジエン類の触媒的ジホウ素化を利用する新規アリルボラン合成法の開発
    科学研究費補助金:
    研究期間 : 1997年 -1998年 
    代表者 : 石山 竜生
  • ジホウ素化合物のクロスカップリングを利用する新規ホウ素官能基導入法の開発
    科学研究費補助金:
    研究期間 : 1996年 
    代表者 : 石山 竜生
  • 遷移金属錯体触媒によるアセチレン類のジホウ素化
    科学研究費補助金:
    研究期間 : 1995年 
    代表者 : 石山 竜生
  • 遷移金属触媒によるアセチレン類のチオボレーション反応
    科学研究費補助金:
    研究期間 : 1994年 -1994年 
    代表者 : 石山 竜生
  • 遷移金属触媒を用いた有機半金属化合物の合成と反応
    科学研究費補助金:
    研究期間 : 1993年 
    代表者 : 石山竜生
  • Syntheses and Reactions of Organo-Metalloid Compounds Using Transition Metal Catalysts
    Grant-in-Aid for Scientific Research
    研究期間 : 1993年

産業財産権

  • オルガノシラン類の製造方法
    JP 2005075807 A2 20050324
  • Proccess for Production of Heteroaryl-Type Boron Compounds with Iridium Catalyst
    WO 200307 4533 A1 20030912
  • Preparation of Aromatic or Aromatic Heterocyclic Silanes from Nonaromatic Disilanes
    JP 2005075807 A2 20050324
  • Proccess for Production of Heteroaryl-Type Boron Compounds with Iridium Catalyst
    WO 200307 4533 A1 20030912
  • 特願2006-246404:有機ケイ素化合物の製造方法  
    石山 竜生


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