Design and Application of Zwitterionic Triazolium Amidate as Hydrogen-Atom Transfer Catalyst
| Project/Area Number |
18H01972
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Nagoya University |
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Principal Investigator |
Ohmatsu Kohsuke 名古屋大学, 工学研究科(WPI), 特任准教授 (00508997)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2020: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2019: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2018: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
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| Keywords | 有機分子触媒 / 水素原子移動 / 光レドックス触媒 / 双性イオン / 1,2,3-トリアゾール / 触媒開発 / ラジカル触媒反応 / ラジカル / イオン性分子触媒 / 水素原子移動反応 / 選択的触媒反応 |
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| Outline of Final Research Achievements |
The catalysis for hydrogen-atom transfer (HAT) is a powerful tool for the direct conversion of inert C-H bonds to C-C bonds. We have designed a zwitterionic 1,2,3-triazolium amidate as an effective modular hydrogen-atom transfer catalyst for photoredox C－H functionalization. This zwitterionic amidate is stable yet amenable to single-electron oxidation for generating a highly reactive amidyl radical. By the combined use with an appropriate Ir-based visible-light photoredox catalyst, we have accomplished efficient catalytic C-H alkylation of a range of C-H nucleophiles. These results provide the new approach to the design of HAT catalysts, and we believe that the judicious exploitation of the structural modularity of zwitterionic amidates holds vast potential for the development of catalyst-controlled selective C-H functionalization methodologies.
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| Academic Significance and Societal Importance of the Research Achievements |
有機分子に遍在する炭素－水素結合を切断し、任意の官能基に変換する手法は、効率的な物質生産の実現に貢献する重要な化学技術である。本研究で開発したトリアゾリウムアミデートによる水素原子移動反応や、メソリティック開裂の能動的制御によるシリルエノールエーテル類のアリル位炭素－水素結合変換反応は、反応基質に存在する極性官能基を残したまま比較的安定な炭素－水素結合を官能基化できるという特徴をもつ。合成化学の分野で長足の進歩を遂げてきた極性反応と組み合わせることで、単純な原料から複雑な化合物を効率的に合成する道を切り拓いたという点に、本研究成果の意義がある。
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Report
(4 results)
Research Products
(23 results)
