Researcher Database
Last Updated :2024/10/02
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Profile and Settings
Affiliation
Profile and Settings
Name (Japanese)
MasudaName (Kana)
YusukeName
201801013139575990
Affiliation
Achievement
Research Interests
Research Areas
Research Experience
- 2021/02 - Today Hokkaido University Faculty of Science
- 2018/03 - 2021/01 Kyoto University Graduate School of Engineering Department of Synthetic Chemistry and Biological Chemistry
- 2017/04 - 2018/02 The University of Tokyo Graduate School of Pharmaceutical Sciences
Education
- 2012/04 - 2017/03 Kyoto University Graduate School of Engineering Department of Synthetic Chemistry and Biological Chemistry
- 2008/04 - 2012/03 Kyoto University Faculty of Engineering School of Industrial Chemistry
Published Papers
- Junpei Shimosato, Masaya Sawamura, Yusuke MasudaOrganic Letters 2024/03/15 [Refereed][Not invited]
- Haruna Mori, Masaki Yoshida, Masaya Sawamura, Yusuke MasudaAsian Journal of Organic Chemistry 2024/02 [Refereed][Not invited]
- Yusuke Masuda, Daichi Ikeshita, Kosuke Higashida, Masaki Yoshida, Naoki Ishida, Masahiro Murakami, Masaya SawamuraJournal of the American Chemical Society 0002-7863 2023/08/21 [Refereed][Not invited]
- Masaki Yoshida, Masaya Sawamura, Yusuke MasudaOrganic Chemistry Frontiers 10 (14) 3654 - 3661 2023 [Refereed][Not invited]
A photocatalytic three-component reaction of alkyltrifluoroborates with two electron-deficient alkenes proceeds in a sequence-selective manner, which can be followed by Wittig olefination to afford γ,δ-unsaturated ketones and esters. - Zhensheng You, Yusuke Masuda, Tomohiro Iwai, Kosuke Higashida, Masaya SawamuraThe Journal of Organic Chemistry 87 (21) 14731 - 14737 0022-3263 2022/10/18 [Refereed][Not invited]
- Masaki Yoshida, Masaya Sawamura, Yusuke MasudaChemCatChem 2022/09/20 [Refereed]
- Daichi Ikeshita, Hiroki Shimura, Sho Miyakawa, Yusuke Masuda, Naoki Ishida, Masahiro MurakamiChemistry Letters 51 (5) 522 - 524 0366-7022 2022/05/05 [Refereed]
- Daichi Ikeshita, Yusuke Masuda, Naoki Ishida, Masahiro MurakamiOrganic Letters 24 (13) 2504 - 2508 2022/04/08 [Refereed]
- Yusuke Ueda, Yusuke Masuda, Tomohiro Iwai, Keisuke Imaeda, Hiroki Takeuchi, Kosei Ueno, Min Gao, Jun-ya Hasegawa, Masaya SawamuraJournal of the American Chemical Society 0002-7863 2022/02/09 [Refereed]
- Yusuke Masuda, Daichi Ikeshita, Masahiro MurakamiChemistry Letters 50 (9) 1691 - 1694 0366-7022 2021/09 [Refereed]
Herein reported is a photocatalytic cycloaddition reaction of triarylphosphines with alkynes. Phosphonium salts of unique bicyclic structures are synthesized through a radical pathway under mild reaction conditions. The phosphonium salts are subjected to the Wittig olefination reaction to afford structurally interesting phosphine oxides. - Masuda, Y., Ito, M., Murakami, M.Chemistry Letters 50 (5) 1030 - 1033 1348-0715 2021/05/05 [Refereed]
- Masuda, Y., Tsuda, H., Murakami, M.Bulletin of the Chemical Society of Japan 94 (6) 1348-0634 2021/04/17 [Refereed]
- Yusuke Masuda, Daichi Ikeshita, Masahiro MurakamiHelvetica Chimica Acta 104 (3) 1522-2675 2021/03 [Refereed]
Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation. - Yusuke Masuda, Hiromu Tsuda, Masahiro MurakamiAngewandte Chemie International Edition 133 (7) 3593 - 3597 1433-7851 2021/02/15 [Refereed]
A unique photoinduced reaction that couples a triarylphosphine, an alkene, and water to produce 2-(cyclohexa-2,5-dienyl)ethylphosphine oxide is reported herein. The alkene inserts into a C(aryl)−P bond of the arylphosphine, the aryl ring is dearomatized into the cyclohexadienyl ring, and the phosphorus is oxidized. The three components are all readily available, and their intermolecular coupling significantly increases molecular complexity. The products formed are applicable to the Wittig olefination. - Masuda, Y., Uno, M., Murakami, M.Organic Letters 23 (21) 1523-7052 2021 [Refereed][Not invited]
- Yusuke Masuda, Misato Ito, Masahiro MurakamiChemistry Letters 49 (11) 1309 - 1311 1348-0715 2020/11/05 [Refereed]
Herein reported is a photoredox-catalyzed oxidative degradation reaction of unprotected aldohexonic acids, which are shortened by one-carbon to the corresponding aldopentoses. Oxygen including aerial oxygen is used as a terminal oxidant. The mild reaction conditions permit even disaccharides to successfully undergo the degradation reaction with the glycosidic bond remaining intact. Quinic acid is also converted to a useful chiral synthetic intermediate. - Yusuke Masuda, Misato Ito, Masahiro MurakamiOrganic Letters 22 (11) 4467 - 4470 1523-7060 2020/06/05 [Refereed]
Herein reported is a dehydrative coupling reaction of alkyl amines with allylic alcohols promoted by co-operation of photoredox and palladium catalysts. A range of homoallylic amines are efficiently synthesized. A mechanistic study suggests that an in situ generated carboxylic acid activates an allylic alcohol to facilitate its oxidative addition onto palladium. - Yusuke Masuda, Katsuhiko Makita, Masahiro MurakamiChemistry Letters 49 (6) 616 - 618 1348-0715 2020/06/05 [Refereed]
Herein reported is a dehydrative allylation reaction of 2-alkylbenzophenones with allylic alcohols promoted by light and palladium. Photoirradiation of 2-alkylbenzophenones generates nucleophilic species which couple with allylic alcohols. Mechanistically, in-situ generated carboxylic acid is likely to activate allylic alcohols to facilitate the palladium-catalyzed allylation reaction. - Yusuke Masuda, Hiromu Tsuda, Masahiro MurakamiAngewandte Chemie 59 (7) 2755 - 2759 1433-7851 2020/02/10 [Refereed]
Unprotected aldoses in water undergo an isomerization reaction via a radical pathway when irradiated with light in the presence of water-soluble benzophenone. Whereas its anomeric carbon (C1) is oxidized to a carboxy group, the hydroxy group on the C2 carbon is replaced by hydrogen. The generated 2-deoxy lactones are readily reduced to the corresponding 2-deoxy aldoses, which are often contained in bioactive compounds. - Naoki Ishida, Yusuke Masuda, Yuuya Imamura, Katsushi Yamazaki, Masahiro MurakamiJournal of the American Chemical Society 141 (50) 19611 - 19615 0002-7863 2019/12/18 [Refereed]
A photoinduced carboxylation reaction of benzylic and aliphatic C-H bonds with CO is developed. Toluene derivatives capture gaseous CO at the benzylic position to produce phenylacetic acid derivatives when irradiated with UV light in the presence of an aromatic ketone, a nickel complex, and potassium tert-butoxide. Cyclohexane reacts with CO to furnish cyclohexanecar-boxylic acid under analogous reaction conditions. The present photoinduced carboxylation reaction provides a direct access from readily available hydrocarbons to the corresponding carboxylic acids with one carbon extension. 2 2 2 - Yusuke Masuda, Katsuhiko Makita, Naoki Ishida, Masahiro MurakamiChemistry – An Asian Journal 14 (23) 4189 - 4192 1861-4728 2019/12/02 [Refereed]
Herein reported is a unique synthetic route of Tofisopam, an anxiolytic drug containing a 2,3-benzodiazepine core structure. 3,4-Dimethoxypropylbenzene and 3,4-dimethoxybenzoic acid, which are both of plant origin, and CO constitute its carbon skeleton. These three renewable substances are united by two C−C bond forming reactions, i.e., a Friedel–Crafts acylation reaction and a photoinduced carboxylation reaction to construct the major carbon framework. Finally, a methyl group is introduced by a Kumada-type cross-coupling reaction to furnish Tofisopam. Various analogs of Tofisopam are readily synthesized by introducing other substituents than a methyl group at the last C−C bond forming step. 2 - Naoki Ishida, Yusuke Masuda, Wenqing Liao, Masahiro MurakamiChemistry Letters 48 (11) 1316 - 1318 1348-0715 2019/11/05 [Refereed]
A photo-assisted three-step procedure to fix carbon dioxide (CO ) onto aryl bromides is reported. In the first photoinduced step, CO is temporarily fixed onto benzophenone to furnish benzilic acid, which is in the second step methylated with (trimethylsilyl)diazomethane. Finally, the obtained methyl ester is subjected to a palladium-catalyzed coupling reaction with aryl bromides. A methoxycarbonyl group is delivered onto an aryl group through a sequence of cleavage/formation of CC bonds to produce aromatic carboxylic esters. 2 2 - Naoki Ishida, Yusuke Masuda, Fangzhu Sun, Yoshiki Kamae, Masahiro MurakamiChemistry Letters 48 (9) 1042 - 1045 1348-0715 2019/09/05 [Refereed]
We herein report that a vicinal diol, which is prepared by a photoinduced dimerization reaction of xanthone, functions as the reductant in a coupling reaction of two organyl halides in the dark. The sterically strained C(sp )C(sp ) σ-bond located in the center of the diol breaks to donate the electrons accommodated therein for the formation of a new CC bond, with the parent xanthone being recovered and recycled for regeneration of the diol. The diol is marked by its preparative convenience and reusability in comparison with other reducing agents that have been employed in analogous reductive coupling reactions. 3 3 - Yusuke Masuda, Naoki Ishida, Masahiro MurakamiChemistry – An Asian Journal 14 (3) 403 - 406 1861-4728 2019/02/14 [Refereed][Not invited]
2-Methylphenyl ketones undergo site-selective acylation at the benzylic position when treated with acid anhydride under UV irradiation in the presence of a palladium catalyst. The benzoyl carbonyl group serves as the photo-directing group so that the ortho benzylic C−H bond is activated site-selectively. - Yusuke MasudaOrganic Syntheses 96 2333-3553 2019 [Refereed][Not invited]
- Naoki Ishida, Yusuke Masuda, Norikazu Ishikawa, Masahiro MurakamiAsian Journal of Organic Chemistry Wiley 6 (6) 669 - 672 2193-5807 2017/03 [Refereed][Not invited]
Benzylic C-H bonds of toluene derivatives are directly arylated with aryl bromides by means of a catalytic system of nickel-bipyridine under irradiation with UV light. The catalyst system is simple and all the components are readily available, and thus, the present system offers a convenient maneuver to shape aryl-benzyl linkages. - Yusuke Masuda, Naoki Ishida, Masahiro MurakamiEuropean Journal of Organic Chemistry 2016 (35) 5822 - 5825 1434-193X 2016/11 [Refereed][Not invited]
An intriguing photoredox system for the homocoupling of aryl halides is reported wherein thioxanthone catalyzes a single-electron transfer from an amine reductant to nickel. - Yusuke Masuda, Naoki Ishida, Masahiro MurakamiChemInform 47 (17) 0931-7597 2016/04 [Refereed][Not invited]
- Naoki Ishida, Yusuke Masuda, Sho Uemoto, Masahiro MurakamiChemistry - A European Journal Wiley 22 (19) 6524 - 6527 0947-6539 2016/03 [Refereed][Not invited]
A photo-induced carboxylation reaction of allylic C-H bonds of simple alkenes with CO2 is prompted by means of a ketone and a copper complex. The unique carboxylation reaction proceeds through a sequence of an endergonic photoreaction of ketones with alkenes forming homoallyl alcohol intermediates and a thermal copper-catalyzed allyl transfer reaction from the homoallyl alcohols to CO2 through C-C bond cleavage. - Yusuke Masuda, Naoki Ishida, Masahiro MurakamiChemInform 46 (47) no - no 0931-7597 2015/11 [Refereed][Not invited]
- Yusuke Masuda, Naoki Ishida, Masahiro MurakamiJournal of the American Chemical Society 137 (44) 14063 - 14066 0002-7863 2015/10 [Refereed][Not invited]
o-Alkylphenyl ketones undergo a C-C bond forming carboxylation reaction with CO2 simply upon irradiation with UV light or even solar light. The reaction presents a clean process exploiting light energy as the driving force for carboxylation of organic molecules with CO2. - Naoki Ishida, David Necas, Yusuke Masuda, Masahiro MurakamiChemInform 46 (43) no - no 0931-7597 2015/10 [Refereed][Not invited]
- Naoki Ishida, Norikazu Ishikawa, Shota Sawano, Yusuke Masuda, Masahiro MurakamiChemInform 46 (25) no - no 0931-7597 2015/06 [Refereed][Not invited]
- Naoki Ishida, David Nečas, Yusuke Masuda, Masahiro MurakamiAngewandte Chemie International Edition 54 (25) 7418 - 7421 1433-7851 2015/05/07 [Refereed][Not invited]
3-Hydroxypiperidine scaffolds were enantioselectively constructed in an atom-economical way by sequential action of light and rhodium upon N-allylglyoxylamides. In a formal sense, the allylic C-H bond was selectively cleaved and enantioselectively added across the ketonic carbonyl group with migration of the double bond (carbonyl-ene-type reaction). - Naoki Ishida, David Nečas, Yusuke Masuda, Masahiro MurakamiAngewandte Chemie 127 (25) 7526 - 7529 0044-8249 2015/05/07 [Refereed][Not invited]
- Ishida, N., Ishikawa, N., Sawano, S., Masuda, Y., Murakami, M.Chemical Communications 51 (10) 1882 - 1885 1364-548X 2015/01 [Refereed][Not invited]
- Yusuke Masuda, Naoki Ishida, Masahiro MurakamiChemistry - An Asian Journal 10 (2) 321 - 324 1861-4728 2014/11 [Refereed][Not invited]
Acylphosphonates are conveniently synthesized from aryl iodides by a palladium-catalyzed reaction with dialkyl phosphites under an atmospheric pressure of carbon monoxide. The reaction demonstrates the first example of the use of phosphorus nucleophiles in related metal-catalyzed carbonylation reactions. - Yusuke Masuda, Maki Hasegawa, Makoto Yamashita, Kyoko Nozaki, Naoki Ishida, Masahiro MurakamiJournal of the American Chemical Society American Chemical Society ({ACS}) 135 (19) 7142 - 7145 0002-7863 2013/05/03 [Refereed][Not invited]
The C-C bond of cyclobutanones undergoes oxidative addition to a T-shape rhodium(I) complex possessing a PBP pincer ligand at room temperature. The remarkable propensity of the rhodium complex for oxidative addition is attributed to the highly electron-donating nature of the boron ligand as well as the unsaturation on the rhodium center. © 2013 American Chemical Society. - Naoki Ishida, Shota Sawano, Yusuke Masuda, Masahiro MurakamiChemInform 44 (13) no - no 0931-7597 2013/03 [Refereed][Not invited]
- Naoki Ishida, Shota Sawano, Yusuke Masuda, Masahiro MurakamiJournal of the American Chemical Society 134 (42) 17502 - 17504 0002-7863 2012/10/11 [Refereed][Not invited]
A rhodium catalyst induced ring opening of benzocyclobutenols with selective cleavage of the C(sp(2))-C(sp(3)) bond adjacent to the hydroxyl group. The site-selectivity markedly contrasted with that of their thermal ring-opening reaction. The rhodium-catalyzed ring opening led to the development of a new alkyne insertion reaction constructing a dihydronaphthalene framework.
Presentations
- Photocatalytic transformation of organophosphorus compounds through distonic radical cation intermediates [Invited]Yusuke MasudaICAT International Symposium on Catalysis 2023 2023/07
- Photocatalytic Synthesis of Organophosphorus Compounds [Invited]Yusuke MasudaThe 15th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-15) 2022/07
- 水中光反応による糖およびホスフィンの革新的分子変換 [Invited]増田侑亮理・工・生命環境学部講演会（関西学院大学） 2022/05
- アリールホスフィンの劇的な⾻格変換を伴う光カップリング反応 [Invited]増田侑亮若手研究者のための有機化学札幌セミナー 2021/11
- Incorporation of Carbon Dioxide into Organic Molecules Utilizing Light as Energy Source [Invited]増田侑亮Reaxys Prize Club シンポジウムin Japan 2017 2017/03
Teaching Experience
- 必修科目演習必修科目演習 Hokkaido University
- 現代有機化学演習現代有機化学演習 Hokkaido University
- 有機化学実験有機化学実験 Hokkaido University
- 自然科学実験自然科学実験 Hokkaido University
Association Memberships
Research Projects
- 日本学術振興会：科学研究費助成事業Date (from‐to) : 2023/04 -2026/03Author : 増田 侑亮
- 創薬を指向したホスホニウム化合物のクリック合成上原記念生命科学財団：研究奨励金Date (from‐to) : 2024/01 -2025/04Author : 増田侑亮
- 日本学術振興会：科学研究費助成事業 挑戦的研究(萌芽)Date (from‐to) : 2022/06 -2025/03Author : 原渕 祐
- 創薬を志向した薬剤分子の光ホスホニオ化反応の開発アステラス病態代謝研究会：研究助成金Date (from‐to) : 2023/01 -2024/12
- Unified Synthesis of Functionalized Alkenes Using Alkenylphosphonium Salts as Key IntermediateJapan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Transformative Research Areas (A)Date (from‐to) : 2022/06 -2024/03Author : 増田 侑亮
- 日本学術振興会：科学研究費助成事業 若手研究Date (from‐to) : 2021/04 -2023/03Author : 増田 侑亮当初の研究計画に従い、水溶性光酸化還元触媒の開発と無保護糖の変換反応に取り組んだ。その結果、配位子にカルボキシ基を有するイリジウム光酸化還元触媒を用いた場合に、水中での無保護糖の光異性化反応が進行し、２―デオキシ糖が得られることを見出した。この反応は、従来のケトン光触媒と紫外光を用いた反応に比べて、可視光を用いる点・生成物が高収率で得られる点・糖酸化体が副生しない点などで優れている。また、水中での糖異性化反応は、既存の疎水性イリジウム光触媒では進行しないことを確かめており、本触媒系が水中光反応を達成する上で重要であることが示された。 水中光反応を検討する際に、アリールホスフィン、アルケン、二酸化炭素の極めて興味深い反応が進行することを見出した。すなわち、水とアセトニトリルの混合溶媒中、二酸化炭素雰囲気下でアリールホスフィンとアルケンの混合物に対してイリジウム光触媒を作用させたところ、シクロプロパン環を含む３環性ホスホニウム塩が得られた。この反応は、アリールホスフィンのベンゼン環のひとつが三員環と五員環が縮環した構造へと脱芳香族化するとともに、リン原子が転位するユニークな反応である。詳細な機構の解析を行ったところ、出発物質から生成物に至るまでに２回の光化学過程を経由していることがわかった。この知見をもとに、アリールホスフィンとアルキンの環化反応による環状ホスホニウム塩の合成およびアリールホスフィンとアルキンのカップリング反応によるアルケニルホスホニウム塩の合成手法を開発した。これらの化合物は続くホスホニウム塩の変換反応によって、多種多様な有機分子へと誘導することが可能であった。 その他、光とパラジウムや銅といった遷移金属触媒を組み合わせた反応の開発にも取り組んでおり、それぞれ新規炭素―リン結合および炭素―炭素結合形成反応として学術論文にまとめた。
- Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Early-Career ScientistsDate (from‐to) : 2019/04 -2021/03Author : Masuda YusukeSugars play an essential role in biological functions, and it is highly desired to develop the methods for efficiently transforming these natural compounds in synthetic organic chemistry. In this study, we developed the direct conversion of unprotected sugars by photo-irradiation in water: Unprotected aldoses such as glucose and ribose were directly transformed to 2-deoxysugars under photo-irradiation by using water-soluble ketone as a catalyst. Furthermore, a water-soluble iridium photocatalyst found to be more efficient for photo-isomerization of sugars, and a wide range of sugars could be converted to the corresponding 2-deoxysugars under mild reaction conditions. Deoxysugars are an important class of natural compounds found in DNA and erythromycin, and they can be directly synthesized from readily available unprotected sugars by the present method.
- 日本学術振興会：科学研究費助成事業 特別研究員奨励費Date (from‐to) : 2017/04 -2020/03Author : 増田 侑亮研究計画に従い、sp3炭素―水素結合のアリール化およびアルキル化反応に関して検討を行った。その結果、ニッケル触媒とヨウ化アルキルの存在下、テトラヒドロフラン(THF)を溶媒とし、グリニヤー反応剤を作用させるこで、THFの炭素―水素結合がアリール化された生成物を低収率で得た。収率向上を目指し、さまざま条件検討を行ったが、大きな改善は見られなかった。 次に、アルコールの炭素―酸素結合官能基化反応に取り組むこととした。検討の結果、プロパルギルアルコール誘導体に対して、ニッケル触媒の存在下グリニヤー反応剤を作用させることで、水酸基の脱離およびプロパルギル基の異性化を伴いながらカップリング反応が進行し、アレンが選択的に生成することを見出した。ニッケル触媒を用いてプロパルギルアルコールからアレンを与える反応としては、これが初めての例である。また、一般にプロパルギル位の置換反応では、アルキンとアレンの混合物を与えることが多い一方、本反応は選択的にアレンを与える点で興味深い。 １―フェニルエタノールに対してパラジウム触媒と銅触媒の存在下、ジボロンを作用させたところ、アルコールの水酸基がホウ素に置換した生成物を与えた。この反応は、２級のベンジルアルコールを直接ホウ素化する手法としては初めての例である。さらに、本反応の不斉反応化を目指して、不斉配位子の検討を行った結果、BINOLから誘導した単座の不斉ホスフィン配位子を用いたときに中程度の鏡像体過剰率で目的のホウ素化体を得ることができた。ラセミ体の官能基を置換することで光学活性な化合物を得る手法は、入手容易な原料から高価値な化合物を合成できる点で非常に優れている。本反応は現在のところ、ラセミ体のアルコールから光学活性な有機ホウ素化合物を一段階で得る唯一の手法であり、有用な反応であると言える。
- Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (S)Date (from‐to) : 2015/05 -2020/03Author : Murakami MasahiroSynthetic transformations of readily available materials such as hydrocarbons were developed by exploiting light and metal catalysts, providing a straightforward access to valued structural motifs. For example, a C-H bond of simple hydrocarbons was cleaved and CO2 was inserted therein to furnish carboxylic acids. Even saturated hydrocarbons, which are generally unreactive, could be used as the substrates. Also developed were stereoselective synthetic pathways from terminal alkynes to homoallylic alcohols with contiguous stereocenters. The process involves (1) introduction of boron groups onto alkynes to prepare alkenylboranes, (2) transposition of the alkene moiety of the alkenylboranes to generate allylboranes, (3) allylation of aldehydes with the generated allylboranes. A variety of homoallylic alcohols were synthesized in an enantio- and diastereo-selective fashion.
- 日本学術振興会：科学研究費助成事業 特別研究員奨励費Date (from‐to) : 2014/04 -2017/03Author : 増田 侑亮昨年度に引き続き、光と遷移金属触媒の協同作用による反応の開発を行った。その結果、ジアリールケトンが光酸化還元触媒として働き、ニッケル触媒による芳香族ハロゲン化物のホモカップリング反応が進行することを見出した。この反応は、これまで用いられてきた貴金属を中心とする光酸化還元触媒と同様の触媒作用を、安価で入手容易なケトンによっても得られることを示した点で意義深い。さらに、フローシステムを用いることで、大スケールの反応に応用することができた。 ニッケル触媒の還元に着目して研究を進めたところ、ピナコール誘導体が還元剤として利用できることを見出した。すなわち、ニッケル触媒による有機ハロゲン化物の還元的カップリング反応が、ピナコール誘導体の存在下進行することがわかった。これにより、これまで用いられてきた亜鉛やマンガンといった金属還元剤に代えて、ピナコール誘導体を利用できることが明らかになった。また、このピナコール誘導体は、ケトンのイソプロピルアルコール溶液に紫外光を照射することで容易に合成できる。 さらに、光照射下ニッケル触媒を用いることで、トルエン誘導体のベンジル位炭素―水素結合を芳香族臭化物によってアリール化できることを見出した。これは、これまで困難であった単純なトルエン誘導体のベンジル位炭素―水素直接アリール化反応であるとともに、触媒としてニッケル錯体のみを必要とするシンプルな反応例である。前述の反応と同様に、高価な光酸化還元触媒を必要としない点で優れている。