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

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 genera...

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Veröffentlicht in:Science (American Association for the Advancement of Science) 2016-02, Vol.351 (6274), p.681-684
Hauptverfasser: Kainz, Quirin M., Matier, Carson D., Bartoszewicz, Agnieszka, Zultanski, Susan L., Peters, Jonas C., Fu, Gregory C.
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Sprache:eng
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Zusammenfassung: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.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.aad8313