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

Kainz, Quirin M. and Matier, Carson D. and Bartoszewicz, Agnieszka and Zultanski, Susan L. and Peters, Jonas C. and Fu, Gregory C. (2016) Asymmetric copper-catalyzed C-N cross-couplings induced by visible light. Science, 351 (6274). pp. 681-684. ISSN 0036-8075. PMCID PMC4770572. doi:10.1126/science.aad8313.

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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.

Item Type:Article
Related URLs:
URLURL TypeDescription Materials CentralArticle
Matier, Carson D.0000-0002-1618-7944
Bartoszewicz, Agnieszka0000-0002-1534-2690
Zultanski, Susan L.0000-0002-4907-9210
Peters, Jonas C.0000-0002-6610-4414
Fu, Gregory C.0000-0002-0927-680X
Alternate Title:Asymmetric copper-catalyzed C–N cross-couplings induced by visible light
Additional Information:© 2016 American Association for the Advancement of Science. Received 10 November 2015; accepted 7 January 2016. Support has been provided by NIH (National Institute of General Medical Sciences, grant R01–GM109194), the Gordon and Betty Moore Foundation, the Alexander von Humboldt Foundation (fellowship for Q.M.K.), and the Bengt Lundqvist Memorial Foundation of the Swedish Chemical Society (fellowship for A.B.). We thank J. M. Ahn, L. M. Henling (Caltech X-Ray Crystallography Facility), M. W. Johnson, N. D. Schley, M. Shahgholi (Caltech Mass Spectrometry Facility), M. K. Takase (Caltech X-Ray Crystallography Facility), N. Torian (Caltech Mass Spectrometry Facility), D. G. VanderVelde (Caltech NMR Facility), and S. C. Virgil (Caltech Center for Catalysis and Chemical Synthesis) for assistance and helpful discussions. Experimental procedures and characterization data are provided in the supplementary materials. Metrical parameters for the structures of compounds 1 to 4 are available free of charge from the Cambridge Crystallographic Data Centre under accession numbers CCDC 1435979, 1435978, 1435977, and 1435980.
Funding AgencyGrant Number
Gordon and Betty Moore FoundationUNSPECIFIED
Alexander von Humboldt FoundationUNSPECIFIED
Swedish Chemical SocietyUNSPECIFIED
Issue or Number:6274
PubMed Central ID:PMC4770572
Record Number:CaltechAUTHORS:20160216-092106614
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64493
Deposited By: Tony Diaz
Deposited On:17 Feb 2016 22:15
Last Modified:06 May 2022 17:34

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