Copper-Catalyzed Highly Efficient and Asymmetric Allylic C–H Oxidation of 3-Aryl-Substituted Terminal Alkenes

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Abstract
Asymmetric allylic C(sp3)-H oxidation of terminal alkenes provides a streamlined process for accessing allylic alcohols and their derivatives; however, it represents a long-standing challenge in the field for several decades. Herein, we disclosed a copper-catalyzed approach for the enantioselective allylic C(sp3)-H oxidation of terminal alkenes, facilitated by introducing a sterically bulky B2Im(C6F5)6 anion. Notably, a wide range of aryl-substituted terminal alkenes were used as limiting reagents, delivering various products with excellent enantioselectivity and regioselectivity (up to 99% ee, >20:1 b/l). Mechanistically, the bulky counteranion was found to be essential for achieving excellent enantioselective control and high catalytic efficiency.
Funding Information
  • Research Grants Council, University Grants Committee (HKUST 16302222)
  • National Key Research and Development Program of China (2021YFA1500100)
  • Youth Innovation Promotion Association of the Chinese Academy of Sciences (Y2022074)
  • National Natural Science Foundation of China (22171279, 22331012, 92256301)
  • Chinese Academy of Sciences (XDB0610000)
  • Tencent Foundation

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