4.8 Article

Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 30, Pages 13468-13474

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c06432

Keywords

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Funding

  1. National Key R&D Program of China [2021YFA1500100]
  2. National Natural Science Foundation of China [91956202, 21790330, 21821002, 22171279]
  3. Science and Technology Commission of Shanghai Municipality [20JC1417000, 21520780100, 19590750400]
  4. Key Research Program of Frontier Science [QYZDJSSW-SLH055]
  5. International Partnership Program of the Chinese Academy of Sciences [121731KYSB20190016]

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The first enantioselective radical trifluoromethylation of benzylic C-H bonds has been achieved using a cooperative photoredox and copper catalysis system. This method provides straightforward access to structurally diverse benzylic trifluoromethylation products with excellent enantioselectivities under mild conditions.
The first enantioselective radical trifluoromethylation of benzylic C-H bonds has been established by a cooperative photoredox and copper catalysis system, providing straightforward access to structurally diverse benzylic trifluoromethylation products in good yields with excellent enantioselectivities under mild conditions. Our method features a broad substrate scope and excellent functional group compatibility. Merging the cooperative photoredox catalysis with copper catalysis is essential for the reaction, where the photoredox catalysis is used for the generation of benzylic radicals from alkyl arenes through a hydrogen atom transfer process and the copper catalysis is used for the enantioselective trifluoromethylation of the benzylic radicals.

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