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Metallaphotoredox Perfluoroalkylation of Organobromides.

ABSTRACT: Ruppert-Prakash type reagents (TMSCF₃, TMSC₂F₅, and TMSC₃F₇) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues.

SUBMITTER: Zhao X

PROVIDER: S-EPMC7722293 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Metallaphotoredox Perfluoroalkylation of Organobromides.

Zhao Xiangbo X MacMillan David W C DWC

Journal of the American Chemical Society 20201109 46

Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abst ...[more]

PMID: 33164534

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