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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:

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

DOI: 10.1021/jacs.0c09977

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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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Key Words

trifluoromethyl arenes, trifluoromethyl alkanes, photochemistry

ID: J48-Y2020