Enantioselective Copper-Catalyzed Alkynylation of Benzylic C-H Bonds via Radical Relay

Journal of the American Chemical Society
Liang FuGuosheng Liu

Abstract

The first enantioselective alkynylation of benzylic C-H bonds via copper-catalyzed radical relay has been established herein, which provides an easy access to structurally diverse benzylic alkynes in good yields with excellent enantioselectivities. A key step for the asymmetric copper-catalyzed radical relay process is the enantioselective capture of a benzylic radical with chiral (Box)CuII-alkynyl species via a inner-sphere pathway. In addition, the reaction displays good functional group tolerance, broad substrate scope and mild conditions. The enantioenriched alkynylation products can be readily transformed into highly valuable synthons, such as chiral terminal alkynes, allenes, alkenes and carboxylic acids. More importantly, our methodology can be applied to the synthesis of bioactive molecule AMG 837.

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Citations

Oct 1, 2020·Chemical Communications : Chem Comm·Shuai LiuYannick Landais
Jan 22, 2021·Nature Communications·Chi ZhangXin-Yuan Liu
Jul 27, 2021·Organic & Biomolecular Chemistry·Huifang LaiDaijun Zha
Oct 10, 2020·Journal of the American Chemical Society·Yuehua ZengHongli Bao
Sep 22, 2020·Journal of the American Chemical Society·Abolghasem BakhodaTimothy H Warren
Sep 1, 2021·Journal of the American Chemical Society·Si-Jie ChenShannon S Stahl
Oct 7, 2021·Chemical Reviews·Liang ChangZhiwei Zuo

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