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Copper-Catalyzed Trifluoromethylation of Alkyl Bromides.

ABSTRACT: Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to Csp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of Csp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromides with trifluoromethyl groups is presented. This operationally simple and robust protocol successfully converts a variety of alkyl, allyl, benzyl, and heterobenzyl bromides into the corresponding alkyl trifluoromethanes.

SUBMITTER: Kornfilt DJP

PROVIDER: S-EPMC7557108 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Trifluoromethylation of Alkyl Bromides.

Kornfilt David J P DJP MacMillan David W C DWC

Journal of the American Chemical Society 20190418 17

Copper oxidative addition into organohalides is a challenging two-electron process. In contrast, formal oxidative addition of copper to Csp2 carbon-bromine bonds can be accomplished by employing latent silyl radicals under photoredox conditions. This novel paradigm for copper oxidative addition has now been applied to a Cu-catalyzed cross-coupling of Csp3-bromides. Specifically, a copper/photoredox dual catalytic system for the coupling of alkyl bromid ...[more]

PMID: 30983333

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