TOHOKU UNIVERSITY Researchers

Research History 4

2026/04 - Present

Tohoku University　Graduate School of Pharmaceutical Sciences & Faculty of Pharmaceutical Sciences　Assistant professor
2023/04 - 2026/03

Graduate School of Science, Kyoto University, Special Research Student
2023/04 - 2026/03

JSPS Research Fellowship for Young Scientists.
2025/06 - 2025/08

RWTH Aachen University, Department of Chemistry, Visiting student

Education 3

Hokkaido University　Graduate School of Life Science

2023/04 - 2026/03
Hokkaido University　Graduate School of Life Science

2021/04 - 2023/03
Hokkaido University　Faculty of Pharmaceutical Sciences

2017/04 - 2021/03

Professional Memberships 3

有機合成化学協会
日本化学会
日本薬学会

Research Interests 3

photocatalyst
organic synthesis
organometallics

Research Areas 4

Life sciences / Pharmaceuticals - chemistry and drug development /
Informatics / Computational science /
Nanotechnology/Materials / Inorganic and coordination chemistry /
Nanotechnology/Materials / Synthetic organic chemistry /

Awards 5

SHIMADZU OMCOS-22 Poster Award

2025/09　22nd International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis　Site-selective C(sp3)-H and Switchable C(sp3)-H/C(sp2)-H Functionalization through Geometry Control of Directing Group
The 23rd Symposium on Organic Chemistry -the Next Generation- Student Lecture Award

2025/05　The Pharmaceutical Society of Japan, Division of Organic Chemistry
優秀ポスター賞

2025/05　Molecular Chirality Research Organization　Cp*Co(III)錯体とキラルカルボン酸を利用した硫黄不斉中心を有するベンゾチアジアジン-1-イミンの触媒的不斉合成
The 15th Otsu Conference Award Fellow

2024/10
日本薬学会北海道支部第148回例会学生優秀発表賞

2021/05　Cp*Co(III)触媒とキラルカルボン酸の組み合わせによるC-Hアミド化を経たチアジアジンの触媒的不斉合成

Papers 9

Photoinduced Selective E/Z Isomerization and Site‐Selective C(sp2)–H Functionalization of Diaryl Methoximes

Yuki Hirata, Masayuki Danjo, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

ChemistryEurope　4　(6)　2026/06/04
Publisher: Wiley
DOI： 10.1002/ceur.70323 　

ISSN： 2751-4765

eISSN： 2751-4765

More details Close

Selective E / Z isomerization of diaryl oxime derivatives, in which the two isomers have similar geometric and electronic characteristics, was achieved using photosensitizers with appropriate triplet energies. We found that suitable substituents can modulate conjugation in methoximes, thereby generating a triplet energy gap between the E and Z isomers. In addition, Z ‐isomer‐enriched methoximes enabled site‐selective C(sp ² )–H functionalization.
Native Amide-Directed C(sp3)–H Alkynylation Using an Electron-Deficient Iridium Catalyst with Pyridone Ligand Assistance

Shunsuke Kimura, Tomoaki Kobayashi, Yuki Hirata, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

Organic Letters　2025/11/20

DOI： 10.1021/acs.orglett.5c04262 　

ISSN： 1523-7060 1523-7052
Site‐Selective C(sp3)−H and Switchable C(sp3)−H/C(sp2)−H Functionalization Enabled by Electron‐Deficient Cp*CF3Ir(III) Catalyst and Photosensitizer

Yuki Hirata, Shunsuke Kimura, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

Angewandte Chemie International Edition　2025/01/02

DOI： 10.1002/anie.202421026 　

ISSN： 1433-7851 1521-3773

More details Close

<jats:title>Abstract</jats:title><jats:p>A site‐selective functionalization of a C(<jats:italic>sp</jats:italic><jats:sup>3</jats:sup>)−H bond was achieved in the presence of an intrinsically more reactive C(<jats:italic>sp</jats:italic><jats:sup>2</jats:sup>)−H bond by controlling the orientation of a directing group via a photo‐induced <jats:italic>E</jats:italic>/<jats:italic>Z</jats:italic> isomerization of an oxime ether. By combining <jats:italic>E</jats:italic>/<jats:italic>Z</jats:italic> isomerization and an electron deficient Cp*<jats:sup>CF3</jats:sup>Ir(III) catalyst, the scope of oxime ethers in C(<jats:italic>sp</jats:italic><jats:sup>3</jats:sup>)−H functionalization was successfully expanded. Based on this strategy, the order of C−H activation was switchable and successive C(<jats:italic>sp</jats:italic><jats:sup>3</jats:sup>)−H/C(<jats:italic>sp</jats:italic><jats:sup>2</jats:sup>)−H and C(<jats:italic>sp</jats:italic><jats:sup>2</jats:sup>)−H/C(<jats:italic>sp</jats:italic><jats:sup>3</jats:sup>)−H double functionalizations were accomplished to construct densely functionalized structures.</jats:p>
Enantioselective C–H amidation of sulfondiimines for the synthesis of 1,2,4-benzothiadiazine-1-imines under cobalt catalysis

Ayami Murata, Tomonori Endo, Yuki Hirata, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

Organic Chemistry Frontiers　2025

DOI： 10.1039/D5QO00355E 　
Cobalt/Photoredox Dual-Catalyzed Cross-Radical Coupling of Alkenes via Hydrogen Atom Transfer and Homolytic Substitution

Yuto Yamaguchi, Yuki Hirata, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

Organic Letters　2024/06/14

DOI： 10.1021/acs.orglett.4c01370 　

ISSN： 1523-7060 1523-7052
Synthesis of Benzo[c]azepine‐1,3(2H)‐diones via C−H Alkylation/Cyclization with α,β‐Unsaturated Acyl Fluorides

Satoko Hosoi, Yuki Hirata, Takumaru Kurihara, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga

Asian Journal of Organic Chemistry　2023/08

DOI： 10.1002/ajoc.202300218 　

ISSN： 2193-5807 2193-5815

More details Close

<jats:title>Abstract</jats:title><jats:p>Transition‐metal‐catalyzed directed C−H functionalization reactions are a powerful method to construct <jats:italic>N</jats:italic>‐heterocycles. However, compared to the formation of five‐ and six‐membered rings, that of seven‐membered rings has been much less explored. Here, the synthesis of benzo[<jats:italic>c</jats:italic>]azepine‐1,3(2<jats:italic>H</jats:italic>)‐diones is described, which are benzene‐fused seven‐membered imides, from hydroxamates and α,β‐unsaturated acyl fluorides via C−H activation using a Cp*Rh(III) catalyst. Under mild reaction conditions, this reaction affords benzo[<jats:italic>c</jats:italic>]azepine‐1,3(2<jats:italic>H</jats:italic>)‐diones that bear a substituent at the 5‐position.</jats:p>
Ruthenium(II)/Chiral Carboxylic Acid Catalyzed Enantioselective C–H Functionalization of Sulfoximines

Long-Tao Huang, Yuki Hirata, Yoshimi Kato, Luqing Lin, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga

Synthesis　2022/11

DOI： 10.1055/a-1588-0072 　

ISSN： 0039-7881 1437-210X

More details Close

<jats:title>Abstract</jats:title><jats:p>Ruthenium(II)-catalyzed enantioselective C–H functionalization reactions of sulfoximines with sulfoxonium ylides are described. The combination of [RuCl2(p-cymene)]2 and a pseudo-C 2-symmetric binaphthyl monocarboxylic acid furnished the S-chiral products in 76:24 to 92:8 er.</jats:p>
Cobalt(III)/Chiral Carboxylic Acid‐Catalyzed Enantioselective Synthesis of Benzothiadiazine‐1‐oxides via C−H Activation

Yuki Hirata, Daichi Sekine, Yoshimi Kato, Luqing Lin, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga

Angewandte Chemie International Edition　2022/07/11

DOI： 10.1002/anie.202205341 　

ISSN： 1433-7851 1521-3773

More details Close

<jats:title>Abstract</jats:title><jats:p>Among sulfoximine derivatives containing a chiral sulfur center, benzothiadiazine‐1‐oxides are important for applications in medicinal chemistry. Here, we report that the combination of an achiral cobalt(III) catalyst and a pseudo‐<jats:italic>C</jats:italic><jats:sub>2</jats:sub>‐symmetric H<jats:sub>8</jats:sub>‐binaphthyl chiral carboxylic acid enables the asymmetric synthesis of benzothiadiazine‐1‐oxides from sulfoximines and dioxazolones via enantioselective C−H bond cleavage. With the optimized protocol, benzothiadiazine‐1‐oxides with several functional groups can be accessed with high enantioselectivity.</jats:p>
Cp*Rh(iii)/boron hybrid catalysis for directed C–H addition to β-substituted α,β-unsaturated carboxylic acids

Ryo Tanaka, Yuki Hirata, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga

Chemical Communications　2022

DOI： 10.1039/d1cc05956d 　

ISSN： 1359-7345 1364-548X

More details Close

<jats:p>The C–H bond addition reaction of 2-phenylpyridine derivatives with α,β-unsaturated carboxylic acids catalyzed by Cp*Rh(<jats:sc>iii</jats:sc>)/BH<jats:sub>3</jats:sub>·SMe<jats:sub>2</jats:sub> is reported.</jats:p>

Show all ︎Show first 5

Presentations 5

配向基の配座制御によるC(sp3)–H/C(sp2)–H結合の選択的官能基化

平田裕己, 木邨俊介, 東田皓介, 吉野達彦, 松永茂樹

次世代を担う有機化学シンポジウム　2025/05
Site-selective and Switchable C(sp3)-H Functionalization through Geometry Control of Directing Group

Yuki Hirata, Shunsuke Kimura, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

2024/09
Site-selective C(sp3)–H functionalization catalyzed by electron-deficient Ir(III) catalyst

Yuki Hirata, Shunsuke Kimura, Kosuke Higashida, Tatsuhiko Yoshino, Shigeki Matsunaga

2024/03
Cp*Co(III)触媒とキラルカルボン酸の組み合わせによるC–Hアミド化を経たチアジアジンの触媒的不斉合成

平田裕己, 関根大地, 加藤佳美, Luqing Lin, 小島正寛, 吉野達彦, 松永茂樹

日本薬学会第143年会　2023/03
Cp*Co(III)触媒とキラルカルボン酸の組み合わせによるC—Hアミド化を経たチアジアジンの触媒的不斉合成

平田裕己, 関根大地, 加藤佳美, Luqing Lin, 小島正寛, 吉野達彦, 松永茂樹

日本薬学会北海道支部第 148 回例会　2021/05

Research Projects 1

連結Cp配位子を基盤とする新規二核Co触媒の創出と遠隔位不斉C-Hアミド化

平田裕己

Offer Organization: 日本学術振興会

System: 科学研究費助成事業

Category: 特別研究員奨励費

Institution: 北海道大学

2023/04/25 - 2026/03/31

More details Close

二核錯体を利用した遠隔位C-H官能基化反応を目指し、二核Co、Rh、Ir錯体の合成を挙げていた。構造が強固に固定されている二核錯体の合成を目指し、配位子の合成を試みたが、本来想定していた配位子の合成は困難であることが判明した。よって、量子化学計算等を用いた緻密な配位子設計を再度行い、当初想定していた通りの配位子を有した二核錯体ではないものの、目標の遠隔位C-H官能基化が達成可能であると考えられる新規二核Co、Rh、Ir錯体3種の合成に成功した。中心金属が異なる3種類の二核錯体は今後の遠隔位C-H官能基化反応を達成するにあたって、検討可能な反応系を格段に増加させることができるという点において、大きな進歩があった。また、二核錯体においては遠隔位の官能基化という位置選択性の発現の達成を目指していたが、異なる位置選択性の発現を達成することにも成功している。高原子価遷移金属錯体を用いたC-H官能基化において、配向基と呼ばれる金属中心に配位して位置選択性を決定する官能基が盛んに利用されている。それらの配向基を利用したC-H官能基化において、現在までC(sp2)-H官能基化が大半を占めており、C(sp3)-H官能基化はC(sp3)-H結合の結合自身の強さや酸性度の高さから報告が少ないのが現状であった。そのため、同化合物内に存在するC(sp2)-H結合とC(sp3)-H結合が、配向基に対して切断可能な位置にある場合、主にC(sp2)-H結合が官能基化され、C(sp3)-H結合のみが官能基化された化合物を得ることは難しい。そこで新たな位置選択性の制御法として配向基の構造に注目することで、C(sp3)-H結合の選択的な活性化を見出した。