Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF₃]

Lisi He, Xinkan Yang and Gavin Chit Tsui*

*Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, Email: gctsuicuhk.edu.hk

L. He, X. Yang, G. C. Tsui, J. Org. Chem., 2017, 82, 6192-6201.

DOI: 10.1021/acs.joc.7b00755

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Abstract

A formal hydrotrifluoromethylation of alkynes is achieved via hydroboration/trifluoromethylation using the inexpensive fluoroform-derived [CuCF₃] reagent. Synthetically useful (E)-alkenyl-CF₃ building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes.

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proposed reaction mechanism

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Key Words

trifluoromethyl alkenes, oxygen

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ID: J42-Y2017