[Report] Asymmetric copper-catalyzed C-N cross-couplings induced by visible light

Thursday, February 11, 2016 - 14:32 in Physics & Chemistry

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. Authors: Quirin M. Kainz, Carson D. Matier, Agnieszka Bartoszewicz, Susan L. Zultanski, Jonas C. Peters, Gregory C. Fu

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