Researcher basic information

• Ph D, Nankai university

• https://researchmap.jp/song_zhiyi?lang=en

• https://jglobal.jst.go.jp/detail?JGLOBAL_ID=201301030995846915
• http://kaken.nii.ac.jp/d/r/80600981.ja.html

• 201301030995846915

• organic synthesis
• organometal
• early transition metal
• C-C bond cleavage
• C-C bong formation
• フルオレン誘導体
• インデン誘導体
• シクロペンタジエニル
• 有機合成
• 遷移金属
• がカップリング

• Nanotechnology/Materials, Synthetic organic chemistry, Organometallics, organic synthesis, polymer material

• Master's degree program, Graduate School of Chemical Sciences and Engineering
• Doctoral (PhD) degree program, Graduate School of Chemical Sciences and Engineering

Research activity information

• Chlorine-free synthesis of axially chiral organophosphorus compounds from white phosphorus
  Xinlei Huangfu; Wei Liu; Zhiyi Song; Junnian Wei; Wen-Xiong Zhang
  Chem, 11, 8, 102496, 102496, Elsevier BV, Aug. 2025
  Scientific journal
• Molecular Moieties Having Pyrene and Carboxylic Acid for the Hydrolysis of Cellulose.
  Nazmul Hasan Md Dostagir; Yusuke Suzuki; Zhiyi Song; Hirokazu Kobayashi; Abhijit Shrotri; Atsushi Fukuoka
  ACS omega, 10, 22, 23058, 23063, 10 Jun. 2025, [International Magazine]
  English, Scientific journal, Hydrolysis of cellulose to glucose is a challenging and crucial step in the field of biomass conversion to fuels and value-added chemicals. Despite the abundance of cellulose, its recalcitrant crystalline structure presents a challenge for its depolymerization to smaller molecules. Conventional heterogeneous catalysts are unable to access glycosidic bonds in cellulose, necessitating cost-consuming pretreatments such as ball-milling. Here, we report a novel approach based on heterogeneous molecular moieties that adsorb on the cellulose surface and hydrolyze cellulose. Three compounds featuring an adsorption domain in the form of a pyrene moiety and vicinal carboxylic acids as an active site were synthesized and tested. By harnessing the cellulose-binding properties of pyrene and the weak acidic functional groups for hydrolysis, these compounds demonstrated enhanced rates of hydrolysis without the need for pretreatment. Glucose yield was increased at a mild temperature of 150 °C in water in the presence of molecular compounds. This work shows a new design idea that can overcome the issues associated with solid acid catalysts for the hydrolysis of crystalline cellulose.
• Computational Prediction and Experimental Confirmation of the Reaction between 1-Lithio-1,3-Butadiene and White Phosphorus Affording Phospholyl Lithium
  Yaqi Zhao; Zhengqi Chai; Zhiyi Song; Junnian Wei; Wen-Xiong Zhang
  Organometallics, 44, 1, 300, 306, American Chemical Society (ACS), 24 Dec. 2024
  Scientific journal
• Flash Communication: Stopping the Movement of Carbon Atoms Traveling in Organic Molecules by Pinacolboryl Substituents
  Tamotsu Takahashi; Masayoshi Bando; Hui Chen; Yang Zheng; Zhiyi Song
  Organometallics, 43, 22, 2851, 2853, American Chemical Society (ACS), 04 Nov. 2024
  Scientific journal
• Formation of Carbon–carbon Double Bond between Cp Ligand and Alkenyl Carbon of Titanacyclopentenes
  Tamotsu Takahashi; Hiroki Nakata; Masayoshi Bando; Zhiyi Song
  Synlett, Georg Thieme Verlag KG, 27 Aug. 2024
  Reactions of bis(cyclopentadienyl)titanacyclopentenes with BiI3 gave coupling products of one Cp ligand and the alkenyl carbons in moderate yields. NMR study of the tetracyanoethylene (TCNE) adduct of the product showed that the coupled Cp ring and the alkenyl carbons were connected by one carbon–carbon double bond. This is in sharp contrast to coupling reactions of one Cp ligand with the diene moiety in bis(cyclopentadienyl)-titanacyclopentadienes, where two carbon–carbon single bonds were formed between those two components to give dihydroindenes or spiro compounds.
• Optically Active Poly(benzene-1,4-diyl)s with Random and Alternating Copolymer Sequences Composed of Chiral and Achiral, Bulky Monomeric Units: A Systematic Study on Side-Chain Bulkiness Effects on Ground-State and Excited-State Chiroptical Properties and Chiral Recognition Ability
  Qingyu Wang; Zhiyi Song; Masayoshi Bando; Takunori Harada; Yoshitane Imai; Hayato Toda; Naofumi Naga; Tamaki Nakano
  Macromolecules, 55, 13, 5390, 5402, American Chemical Society (ACS), 12 Jul. 2022
• Photo racemization of 2,2′-dihydroxy-1,1′-binaphthyl derivatives
  Qingyu Wang; Adriana Pietropaolo; Mariagrazia Fortino; Zhiyi Song; Masayoshi Bando; Naofumi Naga; Tamaki Nakano
  Chirality, 34, 2, 317, 324, Wiley, Feb. 2022
  Scientific journal
• Aggregation-induced chirality amplification of optically active fluorescent polyurethane and a cyclic dimer in the ground and excited states
  Zhiyi Song; a; Hiroyasu Sato; Adriana Pietropaolo; Qingyu Wang; Shuhei Shimoda; Heshuang Dai; Yoshitane Imai; Hayato Toda; Takunori Harada; Yukatsu Shichibu; Katsuaki Konishi; Masayoshi Bando; Naofumi Naga; Tamaki Nakano
  Chem. Commun.,, 58, 7, 1029, 1032, Jan. 2022, [Peer-reviewed]
  English, Scientific journal
• Unexpected structural defects in a main-chain conjugated polymer synthesized through Suzuki-Miyaura cross coupling polymerization
  Yuehui Yuan; Zhiyi Song; Masayoshi Bando; Tamaki Nakano
  Polymer, 226, 123769, 123769, Elsevier BV, Jun. 2021
  English, Scientific journal, Suzuki-Miyaura cross coupling (SMC) copolymerization of 3,8-dibromo-1,10-phenanthroline (PhenBr(2)) and 9,9-dioctylfluorene-2,7-diboronic acid (DOF[B(OH)(2)](2) was conducted aiming to synthesized an alternating copolymer composed of 1,10-phenanthroline-3,8-diyl and 9,9-dioctylfluorene-2,7-diyl units in a mixture of 1,2-dimethoxyethane and water using Pd(PPh3)(4) and K2CO3 as catalysts at different temperatures. Side reactions were unexpectedly found to take place in the reactions at 100 degrees C where hydroxy and carbonyl groups appeared to be introduced probably to 1,10-phenanthroline units. Such reactions were more remarkable in the polymerization than in a model reaction leading to a triad molecule consisting of central 1,10-phenanthroline-3,8-diyl unit connected to two 9,9-dioctylfluorene-2-yl units, suggesting that a longer growing species has a role in such reactions. The extent of side reactions was higher with H2O than with D2O and was negligible with (H2O)-O-18. The polymer with structural defects showed photo absorbance and emission profiles and thermal properties which were remarkably different from those of the alternating copolymer without structural defects.
• A Triad Fluorenone Derivative Bearing Two Imidazole Groups That Switches between Three States by Base and Acid Stimuli
  Yuting Wang; Nabin Maity; Liming Zhao; Maximilian Krämer; Jun-ya Hasegawa; Yukatsu Shichibu; Katsuaki Konishi; Xiaoyuan Wang; Zhiyi Song; Masayoshi Bando; Tamaki Nakano
  Chemistry Letters, 50, 7, 1363, 1367, The Chemical Society of Japan, Apr. 2021
  Scientific journal
• Effect of L-menthol chain-end on the optical rotation, chirality, tacticity and thermal properties of polystyrene prepared by ATRP and polyvinylacetates prepared by RAFT polymerization: A molecular weight dependence study
  Sambhav Vishwakarma; Archana Kumari; Kheyanath Mitra; Shikha Singh; Zhiyi Song; Masayoshi Bando; Tamaki Nakano; Susanta Kumar Sen Gupta; Biswajit Ray
  Materials Today Communications, 26, 101705, 101705, Elsevier BV, Mar. 2021
  Scientific journal, Abstract Two series of L-menthol-tagged homopolymers: one polystyrenes (PSt) and the other polyvinylacetates (PVAc) having different molecular weights have been synthesized via ATRP of styrene, and RAFT polymerization of vinyl acetate, respectively. Optical rotation study has established the magnitude of the optical rotation value for the both polymer series has been found decreasing exponentially with the increase of their molecular weights. CD study has revealed an exponential decrease in the molar ellipiticity values at 235 nm with the increase in the DPs of polymers in both the polymer systems. Formed PSts and PVAcs are atactic and slightly syndiotactic, respectively. With increase in the chain length of the polymers, glass-transition temperature (Tg) values have been found increasing exponentially in both systems. Therefore, living radical polymerization using suitable ATRP initiator or, RAFT agent containing suitable chiral moiety can be useful in inducing chirality in polymers up to high chain length.
• Optically active covalent organic frameworks and hyperbranched polymers with chirality induced by circularly polarized light
  Yuting Wang; Koji Yazawa; Qingyu Wang; Takunori Harada; Shuhei Shimoda; Zhiyi Song; Masayoshi Bando; Naofumi Naga; Tamaki Nakano
  Chemical Communications, 57, 62, 7681, 7684, Royal Society of Chemistry (RSC), 2021
  English, Scientific journal,

  Preferred-handed twist was induced by CPL to covalent organic frameworks (COF’s) and hyperbranched polymers where the internal rotation rate in the COF’s estimated by solid-state NMR was found to affect the chirality induction efficiency.

• Blue circularly polarized luminescent amorphous molecules with single-handed propeller chirality induced by circularly polarized light irradiation
  Zhaoming Zhang; Takunori Harada; Adriana Pietropaolo; Yuting Wang; Yue Wang; Xiao Hu; Xuehan He; Hui Chen; Zhiyi Song; Masayoshi Bando; Tamaki Nakano
  Chemical Communications, 57, 14, 1794, 1797, Royal Society of Chemistry (RSC), Jan. 2021
  Scientific journal,

  Single-handed propeller structure was induced by circularly polarized light irradiation to three molecules with a flat core moiety and twisted periphery groups (wings). The molecules exhibited efficient blue circularly polarized luminescence.

• Pd Nanoparticles-Loaded Vinyl Polymer Gels: Preparation, Structure and Catalysis
  Elsayed Elbayoumy; Yuting Wang; Jamil Rahman; Claudio Trombini; Masayoshi Bando; Zhiyi Song; Mostafa A. Diab; Farid S. Mohamed; Naofumi Naga; Tamaki Nakano
  Catalysts, 11, 1, 137, 137, MDPI AG, Jan. 2021
  Scientific journal, Four vinyl polymer gels (VPGs) were synthesized by free radical polymerization of divinylbenzene, ethane-1,2-diyl dimethacrylate, and copolymerization of divinylbenzene with styrene, and ethane-1,2-diyl dimethacrylate with methyl methacrylate, as supports for palladium nanoparticles. VPGs obtained from divinylbenzene and from divinylbenzene with styrene had spherical shapes while those obtained from ethane-1,2-diyl dimethacrylate and from ethane-1,2-diyl dimethacrylate with methyl methacrylate did not have any specific shapes. Pd(OAc)2 was impregnated onto VPGs and reduced to form Pd0 nanoparticles within VPGs. The structures of Pd0-loaded VPGs were analyzed by XRD, TEM, and nitrogen gas adsorption. Pd0-loaded VPGs had nanocrystals of Pd0 within and on the surface of the polymeric supports. Pd0/VPGs efficiently catalyzed the oxidation/disproportionation of benzyl alcohol into benzaldehyde/toluene, where activity and selectivity between benzaldehyde and toluene varied, depending on the structure of VPG and the weight percentage loading of Pd0. The catalysts were stable and Pd leaching to liquid phase did not occur. The catalysts were separated and reused for five times without any significant decrease in the catalytic activity.
• Optically Active Polymers with Cationic Units Connected through Neutral Spacers: Helical Conformation and Chirality Transfer to External Molecules
  Yuting Wang; Nino Zavradashvili; Yue Wang; Adriana Pietropaolo; Zhiyi Song; Masayoshi Bando; Ramaz Katsarava; Tamaki Nakano
  Macromolecules, 53, 22, 9916, 9928, American Chemical Society (ACS), Dec. 2020
  Scientific journal, Cationic chiral polymers consisting of a chiral “Arg monomeric unit” consisting of two l-arginine moieties joined together through an oxyhexane-1,6-diyloxy spacer unit and achiral “Sp monomeric uni...
• Synthesis of CF2H-Containing Oxime Ethers Derivatives from ClCF2H, tert-Butyl Nitrile and Indoles
  Feb. 2020
• Synthesis and stereochemistry of helical polyurethanes based on 2,2 '-dihydroxy-1,1 '-binaphthyl and diisocyanatobenzenes
  Heshuang Dai; Yukatsu Shichibu; Yoshitane Imai; Nobuyuki Hara; Katsuaki Konishi; Yue Wang; Zhiyi Song; Tamaki Nakano
  POLYMER CHEMISTRY, 11, 6, 1134, 1144, Feb. 2020
  English, Scientific journal
• Cu-Catalyzed C-N Bond Cleavage of 3-Aminoindazoles for C-H Arylation of Enamines
  Nov. 2019
• Polymerization of Bulky of Oxirane Monomers Leading to Polyethers Exhibiting Intramolecular Charge Transfer Interactions
  Maia Merlani; Zhiyi Song; Yuting Wang; Yuehui Yuan; Jiyue Luo; Vakhtang Barbakadze; Bezhan Chankvetadze; Tamaki Nakano
  Macromolecular Chemistry and Physics, 220, 23, Wiley, Nov. 2019
  Scientific journal, AbstractThree novel oxirane monomers, 2‐methoxycarbonyl‐3‐(3,4‐dibenzyloxyphenyl)oxirane (MDBPO), 2‐benzyloxycarbonyl‐3‐(3,4‐dibenzyloxyphenyl)oxirane (BDBPO), and 2‐t‐butyloxycarbonyl‐3‐(3,4‐dibenzyloxyphenyl)oxirane (TBDBPO) are prepared and polymerized using BF3‐OEt2 in CH2Cl2 to yield polyethers. The monomers smoothly lead to polymers under the cationic conditions in spite of the monomers' rather bulky structures. The obtained polymers exhibit characteristic UV spectra with intramolecular charge transfer (ICT) bands through hetero π‐stacked structure formed between the side‐chain carbonyl group and the phenyl group directly connects to the main chain. The relative intensity of the ICT bands is the strongest for poly(TBDBPO) having bulky t‐butyl ester group. This spectral feature is considered to have connection with rigidity of polymer chain. Poly(TBDBPO) having the bulkiest side‐chain group is considered to possess the most rigid chain conformation that can account for its strongest ICT interactions that may occur between the carbonyl group and the phenyl group directly attached to the main chain. The proposed rigid chain conformation of poly(TBDBPO) is supported by the fact that the polymer does not show clear Tg while the other two polymers do.
• Metal-dependent regioselective homocoupling of stannyl- and alkyl-substituted alkynes on group 4 elements. Formation of unsymmetrical titanacyclopentadienes and symmetrical zircona-cyclopentadienes
  Masayoshi Bando; Kiyohiko Nakajima; Zhiyi Song; Tamotsu Takahashi
  Dalton Transactions, 48, 37, 13912, 13915, Royal Society of Chemistry (RSC), Aug. 2019
  

  Homocoupling of stannyl- and alkyl-substituted alkynes with Cp₂TiBu₂ gave unsymmetrical titanacyclopentadienes with >95% regioselectivities, whereas the coupling with Cp₂ZrBu₂ provided symmetrical zirconacyclopentadienes with >93% selectivities.

• Synthesis and photo-induced stereomutation of helical, π-stacked copolymers of dibenzofulvene and menthyl methacrylate
  Jiyue Luo; Yue Wang; Zhiyi Song; Tamaki Nakano
  European Polymer Journal, 118, 71, 77, Elsevier BV, May 2019
  Scientific journal, Abstract Copolymerization of dibenzofulvene (DBF) with (−)-menthyl methacrylate ((1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl methacrylate) (MnMA) prepared from L-(-)-menthol ((1R,2S,5R)-(-)-5-methyl-2-(1-methylethyl)cyclohexanol) and methacrylic chloride was conducted under free radical conditions in toluene using α,α′-azobisisobutylonitrile (AIBN). DBF exhibited much higher reactivity compared with MnMA under all conditions examined in this work, leading to the products comprised mainly of DBF units. NMR, UV, and fluorescence spectral analyses indicated that higher-molar-mass copolymers have completely π-stacked DBF sequences with high conformational regularity while lower-molar-mass copolymers possess both π-stacked and unstacked DBF units in the chain. The ratios of π-stacked and unstacked side-chain fluorene groups of DBF units in excited states were determined by fluorescent emission spectra. The chiral copolymers exhibited circular dichroism (CD) spectra in the wavelength range of absorbance of side-chain fluorene units, suggesting that a preferred left-handed helical conformation was induced by the chirality of MnMA units. In addition, a conformational transformation leading to a loss of optical activity was induced by photo irradiation while the chirality of the copolymers was stable in tetrahydrofuran solution on heating up to 60 °C. The stereomutation was suggested to be a helix-to-random transition.
• Coming Back to the Starting Position of Carbons Traveling in Organic Molecules on Titanium: Merry-Go-Round Reaction
  Masayoshi Bando; Kiyohiko Nakajima; Zhiyi Song; Tamotsu Takahashi
  Organometallics, 38, 4, 731, 734, American Chemical Society (ACS), Feb. 2019
  Traveling of carbon atoms in organic molecules was successfully achieved. The six-membered ring of dihydroindenyl moiety on titanium rotated based on the five-membered ring like a merry-go-round. Two carbons at the bridgehead of the dihydroindenyl moiety and the other three carbons of the five-membered ring were monitored by 13C-labeled experiments. The two carbons at the bridgehead moved to the farthest positions with the rotation of the six-membered ring. The intermediate where the two carbons were located at the farthest positions was isolated and fully characterized. Treatment of the intermediate with azobenzene made the two carbons come back to the starting positions. There is another viewpoint on this reaction. When the six-membered ring is fixed and the movement of three carbons of the five-membered ring of the dihydroindenyl moiety on titanium is focused, it was found that those three carbons moved around the six-membered ring and came back to the starting points.
• Second-Ring Diels-Alder Adducts of Substituted Pentacenes
  Zhiying Jia; Kiyohiko Nakajima; Ken-Ichiro Kanno; Zhiyi Song; Tamotsu Takahashi
  ChemistrySelect, 3, 16, 4298, 4302, Wiley-Blackwell, 30 Apr. 2018, [Peer-reviewed]
  English
• Lithiation of palladated dihydropentacene: A new route for the introduction of substituents from both of electrophiles and nucleophiles to pentacene
  Yanqing Wang; Kiyohiko Nakajima; Zhiyi Song; Tamotsu Takahashi
  Chemical Communications, 54, 10, 1265, 1268, Royal Society of Chemistry, 2018, [Peer-reviewed]
  English
• Formation of a spiro compound via coupling of a cyclopentadienyl ligand with a diene moiety of titanacyclopentadiene
  Masayoshi Bando; Yuki Mizukami; Kiyohiko Nakajima; Zhiyi Song; Tamotsu Takahashi
  DALTON TRANSACTIONS, 46, 47, 16408, 16411, Dec. 2017, [Peer-reviewed]
  English
• Formation A Spiro[4,4]nona-1,3,6-triene by the Reaction of Bis(cyclopentadienyl)titanacyclopentadienes with Bismuth(III) Chloride
  song zhiyi
  Dalton Transactions, 46, 16408, 16411, 2017, [Peer-reviewed]
  English, Scientific journal
• Formation of Seven-Membered Carbocycles via 7-endo Mode Cyclization of Lithioheptatrienes
  Ken-ichiro Kanno; Efi Igarashi; Yuki Mizukami; Kiyohiko Nakajima; Zhiyi Song; Tamotsu Takahashi
  ORGANIC LETTERS, 18, 24, 6217, 6219, Dec. 2016, [Peer-reviewed]
  English, Scientific journal
• Separation of Five Linearly Aligned Carbons into Two-Carbon and Three-Carbon Groups on Titanium
  Zhiyi Song; Yi-Fang Hsieh; Kiyohiko Nakajima; Ken-ichiro Kanno; Tamotsu Takahashi
  ORGANOMETALLICS, 35, 8, 1092, 1097, Apr. 2016, [Peer-reviewed]
  English
• Halogen Exchange Reaction of Aliphatic Fluorine Compounds with Organic Halides as Halogen Source
  Yuki Mizukami; Zhiyi Song; Tamotsu Takahashi
  ORGANIC LETTERS, 17, 24, 5942, 5945, Dec. 2015, [Peer-reviewed]
  English
• Coupling of Titanacyclopentadienes with a Cp Ligand and Elimination of One Substituent
  Yuki Mizukami; Haijun Li; Kiyohiko Nakajima; Zhiyi Song; Tamotsu Takahashi
  ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 53, 34, 8899, 8903, Aug. 2014, [Peer-reviewed]
  English, Scientific journal
• MnI2-catalyzed Dimerization of 2-Hydroxyanthracene
  Sicheng Zhang; Yanqing Wang; Zhiyi Song; Kiyohiko Nakajima; Tamotsu Takahashi
  CHEMISTRY LETTERS, 42, 7, 697, 699, Jul. 2013, [Peer-reviewed]
  English, Scientific journal

  
  Download
• APPLICATION OF ZIRCONACYCLOPENTADIENES (METALLA-HETEROCYCLES) AND CROSS-COUPLING FOR THE CONVENIENT PREPARATIVE METHOD OF 6,13-DISUBSTITUTED PENTACENE
  Zhiying Jia; Shi Li; Kiyohiko Nakajima; Ken-ichiro Kanno; Zhiyi Song; Tamotsu Takahashi
  HETEROCYCLES, 86, 2, 1495, 1506, Dec. 2012, [Peer-reviewed]
  English, Scientific journal
• Synthesis of Co-oligomers of Thiophene Derivatives from Oligoynes via Zirconacyclopentadiene
  Debabrata Payra; Zhiyi Song; Ken-ichiro Kanno; Tamotsu Takahashi
  CHEMISTRY LETTERS, 40, 12, 1447, 1449, Dec. 2011, [Peer-reviewed]
  English, Scientific journal
• Coupling Reaction of a Cyclopentadienyl Ligand with a Dienyl or Alkenyl Moiety on Titanocene
  Zhiyi Song; Yi-Fang Hsieh; Ken-ichiro Kanno; Kiyohiko Nakajima; Tamotsu Takahashi
  ORGANOMETALLICS, 30, 4, 844, 851, Feb. 2011, [Peer-reviewed]
  English, Scientific journal
• Once Cleaved C-C Bond Was Reformed: Reversible C-C Bond Cleavage of Dihydroindenyltitanium Complexes
  Tamotsu Takahashi; Zhiyi Song; Yi-Fang Hsieh; Kiyohiko Nakajima; Ken-ichiro Kanno
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 130, 46, 15236, +, Nov. 2008, [Peer-reviewed]
  English
• Synthesis and properties of photochromic biindenylidenedione derivatives containing thiophene groups, and new insights into the reaction of 2,2 '-biindanylidene-1,1 ',3,3 '-tetraone with Grignard reagent
  Juyan Liu; Jie Han; Zhiyi Song; Yongheng Wei; Meili Pang; Jiben Meng
  JOURNAL OF MOLECULAR STRUCTURE, 891, 1-3, 214, 220, Nov. 2008, [Peer-reviewed]
  English, Scientific journal
• Once Cleaved C−C Bond Was Reformed: Reversible C−C Bond Cleavage of Dihydroindenyltitanium Complexes
  Tamotsu Takahashi; Zhiyi Song; Yi-Fang Hsieh; Kiyohiko Nakajima; Ken-ichiro Kanno
  Journal of the American Chemical Society, 130, 46, 15236, 15237, American Chemical Society (ACS), 25 Oct. 2008
  Scientific journal
• Effect of substituents at 1,4-positions of polycyclic aromatic compounds and preparation of 2,3-difunctionalized pentacenes and naphthacenes
  Shi Li; Lishan Zhou; Zhiyi Song; Fengyu Bao; Ken-Ichiro Kanno; Tamotsu Takahashi
  HETEROCYCLES, 73, 1, 519, +, Dec. 2007, [Peer-reviewed]
  English
• 1-chloro-4,5,6,7-tetraalkyldihydroindene formation by reaction of bis(cyclopentadienyl)titanacyclopentadienes with titanium chloride
  Tamotsu Takahashi; Zhiyi Song; Kimihiko Sato; Yuichi Kuzuba; Kiyohiko Nakajima; Ken-ichiro Kanno
  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 129, 38, 11678, +, Sep. 2007, [Peer-reviewed]
  English
• Preparation of partially substituted 1-halo- and 1,4-dihalo-1,3-dienes via reagent-controlled desilylation of halogenated 1,3-dienes.
  Zhenfeng Xi; Zhiyi Song; Guangzhen Liu; Xiaozhong Liu; Tamotsu Takahashi
  The Journal of organic chemistry, 71, 8, 3154, 8, American Chemical Society (ACS), 14 Apr. 2006, [International Magazine]
  English, Depending on the desilylation reagents used, 1-halo-1,4-bis(trimethylsilyl)-1,3-butadienes afforded either 1-halo-1-trimethylsilyl-1,3-butadienes or 1-halo-4-trimethylsilyl-1,3-butadienes in excellent yields with excellent selectivity, respectively, when treated with CF3COOH or with NaOMe. These monosilylated 1,3-butadiene products could be further desilylated to generate their corresponding halobutadienes via the above reagent-controlled desilylation reaction. When 1,4-dihalo-1,4-bis(trimethylsilyl)-1,3-dienes were treated with MeONa/MeOH at room temperature, desilylation of both of the two trimethylsilyl groups took place to afford their corresponding 1,4-dihalo-1,3-dienes in excellent yields. The commonly used desilylation reagent CF3COOH did not work for these dihalobutadienes.
• Preparation of vinyl allenes from 1-lithio-1,3-dienyl phosphine oxides and aldehydes by the Wittig-Horner reaction.
  Zhenfeng Xi; Wen-Xiong Zhang; Zhiyi Song; Weixin Zheng; Fanzhi Kong; Tamotsu Takahashi
  The Journal of organic chemistry, 70, 22, 8785, 9, American Chemical Society (ACS), 28 Oct. 2005, [International Magazine]
  English, [reaction: see text] Vinyl allenes were prepared in high yields by the Wittig-Horner reaction of 1-lithio-1,3-dienyl phosphine oxides with aldehydes. 1-Lithio-1,3-dienyl phosphine oxides were generated in situ from lithiation of 1-iodo-1,3-dienyl phosphine oxides, which were obtained by iodination of alpha-phosphinozirconacyclopentadienes. As a whole, a vinyl allene is synthesized from two different alkynes and one aldehyde.

• 炭素系触媒モデル分子による結晶セルロースの加水分解
  福岡淳; DOSTAGIR Nazmul; 鈴木悠介; 宋志毅; 小林広和; SHROTRI Abhijit, 触媒討論会予稿集(CD-ROM), 134th, 2024
• Cu-catalyzed C–N bond cleavage of 3-aminoindazoles for the C–H arylation of enamines
  Ya Wang; Qiuling Song; Zhiyi Song; Tamaki Nakano; Yao Zhou, Organic Chemistry Frontiers, 7, 25, 29, 01 Jan. 2020
  We have presented a novel Cu-catalyzed stereoselective C–H arylation of enamines by using 3-aminoindazoles arylating agents via oxidative cleavage of two C–N bonds., Royal Society of Chemistry (RSC)
• Synthesis of CF₂H‐Containing Oxime Ethers Derivatives from ClCF₂H, tert‐Butyl Nitrile and Indoles
  Hua Huang; Zhiyi Song; Qiuling Song; Tamaki Nakano; Xingxing Ma; Jianke Su, Chinese Journal of Chemistry, 38, 63, 68, 23 Nov. 2019
  Summary of main observation and conclusionA new and intriguing methodology to access various O‐difluoromethylation oxime compounds from ClCF2H, TBN and indoles is developed under mild reaction conditions. This strategy can suppress N‐difluoromethylation of indoles successfully, in which there are two different active species (:CF2 and ·NO) while indoles are unprotected, featuring simple operation and radical involvement., Wiley
• 抗酸化機能を有するπ-スタック型ビニルポリマーの合成と構造
  浅田駿太; 浅田駿太; 王ヤン; 王ヤン; 宋志毅; 宋志毅; 中野環; 中野環, 高分子学会北海道支部研究発表会講演要旨集, 53rd, 2019
• 軸不斉を有するポリ(ナフタレン-1,4-ジイル)の合成と構造
  孫歌; 孫歌; 宋志毅; 宋志毅; 中野環; 中野環, 高分子学会北海道支部研究発表会講演要旨集, 53rd, 2019
• 2,2’-ビピリジル基を側鎖に有するビニル高分子配位子の合成および触媒反応への応用
  葛西聡馬; 葛西聡馬; 王ヤン; 王ヤン; 宋志毅; 宋志毅; 中野環; 中野環, 高分子学会北海道支部研究発表会講演要旨集, 53rd, 2019
• チタン上での炭素-炭素結合切断と物質変換
  坂東正佳; 栗海軍; 中島清彦; 宋志毅; 高橋保, 万有生命科学振興国際交流財団札幌シンポジウム, 28th, 2016
• チタンノセン触媒を用いたアルキルフッ素化合物のハロゲン交換反応の開発
  宋志毅; 水上雄貴; 中島清彦; 高橋保, 触媒討論会討論会A予稿集, 118th, 2016
• チタン錯体上で起こる炭素-炭素結合切断反応
  水上雄貴; 宋志毅; 中島清彦; 高橋保, 万有生命科学振興国際交流財団札幌シンポジウム, 26th, 2014
• チタノセン錯体を用いた炭素-炭素結合切断を伴う新規反応の開発研究
  水上雄貴; 中島清彦; 宋志毅; 高橋保, 化学系学協会北海道支部冬季研究発表会講演要旨集, 2012, 2012
• ヘプタトリエン誘導体の分子内環化反応
  水上雄貴; 五十嵐絵里; 宋志毅; 高橋保, 日本化学会北海道支部夏季研究発表会講演要旨集, 2011, 2011
• Synthesis of stereo-defined 1,1,4,4-tetrahalo- and 1,1,4,4-mixed-tetrahalo-1,3-butadienes
  Hui-Jun Zhang; Zhiyi Song; Chao Wang; Christian Bruneau; Zhenfeng Xi, Tetrahedron Letters, 49, 4, 624, 627, Jan. 2008
  Elsevier BV
• 低原子価前周期遷移金属を触媒に用いた炭素-ハロゲン結合の活性化反応
  菅野研一郎; 賀建軍; 郭海卿; 中島清彦; 宋志毅; 高橋保, 触媒討論会討論会A予稿集, 100th, 2007
• The helical structure of a photochromic spironaphthopyran
  Rui Sun; Zhiyi Song; Jiben Meng; Teruo Matsuura; Qi Ji, Journal of Molecular Structure, 655, 31, 35, 01 Jul. 2003
  The title compound, 6 0 -ethoxycarbonylspiro(indoline-2,2 0 -[2H-1]-naphthopyran) (Compound I), was synthesized and the structure was determined by X-ray diffraction. Introduction of an ethoxycarbonyl group in the 6 0 -position of the indoline moiety affects the whole arrangement of molecular self-assembly. The carbonyl oxygen atom is involved in hydrogen bond, through which the stacking arrangement in the crystal forms a helical structure. q 2003 Elsevier Science B.V. All rights reserved., Elsevier BV
• An unexpected participation of oxygen in a novel synthesis of [2,2′-bi-1H-indene]-3,3′-dialkyl-3,3′-dihydroxy-1,1′-diones
  Lili Xu; Huaming Huang; Zhiyi Song; Jiben Meng; Teruo Matsuura, Tetrahedron Letters, 43, 41, 7435, 7439, Oct. 2002
  Abstract This paper describes, for the first time, a short synthetic procedure for [2,2′-bi-1H-indene]-3,3′-dialkyl-3,3′-dihydroxy-1,1′-diones ( 1a–f ). The key feature of this synthetic method lies in the participation of oxygen when the intermediate arises from the nucleophilic addition of alkylmagnesium bromide to 2,2′-biindanylidene-1,1′,3,3′-tetraone. The background leading to the development of this synthesis is discussed, together with the proposal of a novel reaction mechanism. The structures of all the new compounds have been determined by X-ray crystallography., Elsevier BV

• Science of Synthesis, Knowledge Updates
  song zhiyi; Takahashi Tamotsu, Grignard Reactions with Transition Metals
  Georg Thieme Verlag KG, Jan. 2013, [Joint work]

• 大学院共通授業科目（一般科目）：自然科学・応用科学, 2024年, 修士課程, 大学院共通科目
• 応用化学特別講義, 2024年, 修士課程, 総合化学院
• 先端総合化学特論Ⅱ, 2024年, 博士後期課程, 総合化学院

• THE CHEMICAL SOCIETY OF JAPAN

• Depolymerization of crystalline cellulose by solid catalysts
  Grants-in-Aid for Scientific Research
  01 Apr. 2021 - 31 Mar. 2024
  福岡 淳; 小林 広和; 宋 志毅
  本研究の目的は、結晶セルロースを加水分解できる固体触媒を開発することである。そのためにトップダウン型とボトムアップ型の触媒設計を用いる。本年度はトップダウン型アプローチとして、カーボンナノチューブなどの炭素材料を切り開き、シート状にした材料にカルボキシ基を導入した固体触媒を調製するために、文献調査を行った。また、活性炭を固体触媒として用いた結晶セルロースの加水分解を行った。無触媒や酸点がない活性炭を触媒として用いた場合、グルコース収率は1%未満となりほとんど反応しなかった。しかし、触媒として酸点を持つ空気酸化活性炭(AC-Air)やグラフェンオキシドを用いたところグルコース収率が5-10%程度に向上した。この結果から、比較的反応しやすいセルロース表面部分でのみ加水分解が起こっており、内部まで反応が進まないことが低収率の原因であると考えられる。さらに、ボトムアップ型のアプローチとして、ピレンユニットと酸点を持った分子触媒の合成を行った。4-ブロモフタル酸と1-ピレンボロン酸の鈴木カップリングにより、ピレンとフタル酸を併せもつPyrene-COOHを合成した。ここでカルボキシル基はメタ・パラ位の位置をもつことを確認した。Pyrene-COOHを触媒として結晶セルロースの反応を行うとグルコース収率は3.2％となり、フタル酸を用いると収率が6.5%となったことから、Pyrene-COOHはセルロースに吸着して作用している可能性があるものの、セルロースの加水分解はほとんど進行しないことが分かった。これは、触媒のカルボキシ基とセルロースのグリコシド結合の接触が限定的であることが原因であると思われる。
  Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 21H01708
• Construction of chiral macromolecular structure through controlled chemical bond rotation by circularly polarized light irradiation
  Grants-in-Aid for Scientific Research
  01 Apr. 2019 - 31 Mar. 2022
  Nakano Tamaki
  The chirality induction method based on chirality of circularly polarized light (CPL) was applied for linear polymers, covalent organic framework (COF) with regular, inner branching, and functional small molecules. A polynaphthalene derivative, a linear polymer, was found to be induced different types of chiral structure through the asymmetric polymerization method and through the CPL irradiation method. Also, the CPL irradiation method led COFs composed of benzene rings to optically active materials with preferred-handed twist around single bonds connecting benzene rings. Furthermore, a series of blue-light emitting small molecules were induced chirality at high efficiency through the CPL irradiation method, and the resulting optically active materials were found to emit circularly polarized luminescence at high anisotropy in blue color, which make them good candidates of blue-CPL-emitting OLED.
  Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 19H02759
• Condensation of Alkynes with Cyclopentadiene via Titanacyclopentadiene Complexes
  Grants-in-Aid for Scientific Research
  2011 - 2012
  SONG Zhiyi
  Titanocene dichloride reacted with two equiv of alkynes to form bis(cyclopentadienyl)titanacyclopentadiene complexes in excellent yields. Subsequently, addition of azobenzene, in ‘one-pot’ manner, led to the formation of indene derivatives inhigh yields. Various alkynes were applicable for the coupling reaction withcyclopentadienyl ligand. When benzene or polyarene bridged diynes were employed, thecorresponding cyclopentadiene-fused acenes were obtained in good yields. These indeneproducts were treated with BuLi and ZrCl4successively to give bis(indenyl)zirconocenedichloride derivatives in good yields.
  Japan Society for the Promotion of Science, Grant-in-Aid for Young Scientists (B), Hokkaido University, 23750097