Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes

Yi-Fei Yang, Jin-Hong Lin* and Ji-Chang Xiao*

*SIOC, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, China, Email: jlinsioc.ac.cn, jchxiaosioc.ac.cn

Y.-F. Yang, J.-H. Lin, J.-C. Xiao, Org. Lett., 2021, 23, 9277-9282.

DOI: 10.1021/acs.orglett.1c03630

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Abstract

The use of TFSP, a readily available trifluoromethylation reagent prepared from DMAP and Tf₂O, enables a general method for the hydrotrifluoromethylation of styrenes under photoredox catalysis without polymerization. The substrate scope was further extended to unactivated alkenes, acrylates, acrylamides, and vinyl-heteroatom-substituted alkenes.

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proposed mechanism (2 = TFSP)

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Key Words

trifluoromethyl alkanes, β-trifluoromethyl amines, photochemistry, Hantzsch ester, triphenylsilane

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ID: J54-Y2021