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Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex.

ABSTRACT: A well-defined copper complex bearing iminosemiquinone ligands performs single electron reduction of an electrophilic CF3+ source into CF?3 radicals. This redox behavior is enabled by the ligand which shuttles through two different redox states (iminosemiquinone and iminobenzoquinone) while the copper center is preserved as a Cu(ii). This system was used in the trifluoromethylation of silyl enol ethers, heteroaromatics and in the hydrotrifluoromethylation of alkynes. This is the first example of cooperative redox catalysis for the controlled generation of CF?3 radicals.

SUBMITTER: Jacquet J

PROVIDER: S-EPMC5968567 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Redox-ligand sustains controlled generation of CF3 radicals by well-defined copper complex.

Jacquet Jérémy J Blanchard Sébastien S Derat Etienne E Desage-El Murr Marine M Fensterbank Louis L

Chemical science 20151203 3

A well-defined copper complex bearing iminosemiquinone ligands performs single electron reduction of an electrophilic CF3+ source into CF˙3 radicals. This redox behavior is enabled by the ligand which shuttles through two different redox states (iminosemiquinone and iminobenzoquinone) while the copper center is preserved as a Cu(ii). This system was used in the trifluoromethylation of silyl enol ethers, heteroaromatics and in the hydrotrifluoromethylation of alkynes. This i ...[more]

PMID: 29899928

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