Asymmetric copper-catalyzed C-N cross-couplings induced by visible light
Author(s) -
Quirin M. Kainz,
Carson D. Matier,
Agnieszka Bartoszewicz,
Susan L. Zultanski,
Jonas C. Peters,
Gregory C. Fu
Publication year - 2016
Publication title -
science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 12.556
H-Index - 1186
eISSN - 1095-9203
pISSN - 0036-8075
DOI - 10.1126/science.aad8313
Subject(s) - copper , catalysis , ruthenium , iridium , photochemistry , chemistry , ligand (biochemistry) , alkyl , visible spectrum , ultraviolet , organic chemistry , materials science , biochemistry , receptor , optoelectronics
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.
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