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Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay

Liang Fu, Song Zhou, Xiaolong Wan, Pinhong Chen, Guosheng Liu*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: gliumail.sioc.ac.cn

L. Fu, S. Zhou, X. Wan, P. Chen, G. Liu, J. Am. Chem. Soc., 2018, 140, 10965-10969.

DOI: 10.1021/jacs.8b07436 (free Supporting Information)


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Abstract

An enantioselective copper-catalyzed trifluoromethylalkynylation of styrenes affords structurally diverse CF3-containing propargylic compounds in good yield with excellent enantioselectivities under very mild conditions via a radical relay process. The reaction offers wide substrate scope and good functional group tolerance. The trifluoromethylalkynylated products can be converted into synthetically useful chiral terminal alkynes, allenes, and Z-alkenes.

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Key Words

trifluoromethylation, alkynylation


ID: J48-Y2018