Development of novel reactions using carbonyls as latent nucleophiles
| Project/Area Number |
18H01971
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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 | Kanazawa University |
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Principal Investigator |
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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: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
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| Keywords | ラジカル反応 / カルベン触媒 / 銅触媒 / 有機触媒 / 不斉触媒 / 触媒・化学反応プロセス / 触媒・化学プロセス |
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| Outline of Final Research Achievements |
The researcher found a radical NHC catalysis enabling decarboxylative cross-coupling reactions of tertiary/secondary, redox-active esters derived from alkyl carboxylic acids with aldehydes to generate ketones. Additionally, the radical NHC catalysis could be employed with the alkylacylation of acrylonitriles, acylates and styrenes with redox esters obtained from tertiary alkyl carboxylic acids and aldehydes, via a radical relay mechanism.
The researcher achieved reductive umpolung using a copper catalyst and a silylboronate to convert an aldehyde to a nucleophilic α-silyloxyalkylcopper(I) species. The α-silyloxyalkylcopper(I) species, generated via addition of the silylcopper(I) species to an aldehyde followed by [1,2]-Brook rearrangement, could react with various electrophiles to afford a series of alcohol derivatives.
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| Academic Significance and Societal Importance of the Research Achievements |
本研究によって見出された分子変換反応により、多様な有機分子へのアプローチにおいて柔軟性が格段に増すと考えられる。そして、従来の変換手法に比べて圧倒的な省資源、低エネルギー、低環境負荷、低コスト化を可能とする理想的な変換プロセスに繋げることができる。
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Report
(4 results)
Research Products
(112 results)
