4.8 Article

Enantioselective Copper-Catalyzed Trifluoromethylation of Benzylic Radicals via Ring Opening of Cyclopropanols

Journal

CHEM
Volume 6, Issue 9, Pages 2407-2419

Publisher

CELL PRESS
DOI: 10.1016/j.chempr.2020.07.003

Keywords

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Funding

  1. National Natural Science Foundation of China (NFSC) [21532009, 21790330, 91956202, 21821002, 21761142010]
  2. Science and Technology Commission of Shanghai Municipality [17JC1401200, 19590750400]
  3. Strategic Priority Research Program [XDB20000000]
  4. Key Research Program of Frontier Science [QYZDJSSWSLH055]
  5. Chinese Academy of Sciences [121731KYSB20190016]

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The asymmetric trifluoromethylation of aryl-substituted cyclopropanols via a radical ring-opening pathway is reported herein, which provides an easy and straightforward access to structurally diverse beta-CF3 ketones in good yields and excellent enantioselectivities under very mild conditions. Critical to the success of the copper-catalyzed radical relay is that a benzylic radical intermediate can be enantioselectively trapped by reactive (L*)(CuCF3)-C-II. In addition, a novel quinolinyl-containing bisoxazoline ligand plays a significant role in the asymmetric trifluoromethylation.

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