Copper-Catalyzed anti-Selective Radical 1,2-Alkylarylation of Terminal Alkynes

Jun-Bin Tang, Jun-Qian Bian, Yu-Shuai Zhang, Yong-Feng Cheng, Han-Tao Wen, Zhang-Long Yu, Zhong-Liang Li, Qiang-Shuai Gu*, Guo-Qiang Chen* and Xin-Yuan Liu*

*Southern University of Science and Technology, Shenzhen 518055; Shenzhen University, Shenzhen 518071, China, Email: guqssustech.edu.cn, gqchenszu.edu.cn, liuxy3sustech.edu.cn

J.-B. Tang, J.-Q. Bian, Y.-S. Zhang, Y.-F. Cheng, H.-T. Wen, Z.-L. Yu, Z.-L. Yu, Z.-L. Li, Q.-S. Gu, G.-Q. Chen, X.-Y. Liu, Org. Lett., 2022, 24, 2536-2540.

DOI: 10.1021/acs.orglett.2c00692

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Abstract

A copper-catalyzed highly anti-selective radical 1,2-alkylarylation of terminal alkynes with aryl boronic acids and alkyl bromides providesg facile access to various stereodefined trisubstituted alkenes in high yield under mild reaction conditions. The reaction exhibits high compatibility with a wide range of terminal alkynes and diverse aryl boronic acids.

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proposed mechanism

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Key Words

arylation, alkylation, substituted esters, multicomponent reactions

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ID: J54-Y2022