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Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.

ABSTRACT: Despite a well-developed and growing body of work in copper catalysis, the potential of copper to serve as a photocatalyst remains underexplored. Here we describe a photoinduced copper-catalyzed method for coupling readily available racemic tertiary alkyl chloride electrophiles with amines to generate fully substituted stereocenters with high enantioselectivity. The reaction proceeds at -40°C under excitation by a blue light-emitting diode and benefits from the use of a single, Earth-abundant transition metal acting as both the photocatalyst and the source of asymmetric induction. An enantioconvergent mechanism transforms the racemic starting material into a single product enantiomer.

SUBMITTER: Kainz QM

PROVIDER: S-EPMC4770572 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.

Kainz Quirin M QM Matier Carson D CD Bartoszewicz Agnieszka A Zultanski Susan L SL Peters Jonas C JC Fu Gregory C GC

Science (New York, N.Y.) 20160201 6274

Despite a well-developed and growing body of work in copper catalysis, the potential of copper to serve as a photocatalyst remains underexplored. Here we describe a photoinduced copper-catalyzed method for coupling readily available racemic tertiary alkyl chloride electrophiles with amines to generate fully substituted stereocenters with high enantioselectivity. The reaction proceeds at -40°C under excitation by a blue light-emitting diode and benefits from the use of a single, Earth-abundant tr ...[more]

PMID: 26912852

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