Metallaphotoredox Perfluoroalkylation of Organobromides

Xiangbo Zhao and David W. C. MacMillan*

*Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States, Email: dmacmillprinceton.edu

X. Zhao, D. W. C. MacMillan, J. Am. Chem. Soc., 2020, 142, 19480-19486.

DOI: 10.1021/jacs.0c09977

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Abstract

A mild, copper-catalyzed cross-coupling of Ruppert-Prakash type reagents (TMSCF₃, TMSC₂F₅, and TMSC₃F₇) with aryl and alkyl bromides provides a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation enables also the late-stage functionalization of several drug analogues.

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[Ir(Fmppy)2(phen)](PF6)

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Key Words

trifluoromethyl arenes, trifluoromethyl alkanes, photochemistry

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ID: J48-Y2020