Journal
ACS CATALYSIS
Volume 7, Issue 10, Pages 7008-7013Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02659
Keywords
asymmetric catalysis; photoredox; coupling; mechanism; DFT; organocatalysis
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Funding
- Marie Sklodowska-Curie action [291787-ICIQ-IPMP]
- ICIQ International PhD Fellowship Programme
- MINECO [CTQ2015-69136-R]
- ICIQ Foundation
- MINECO through the Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- CELLEX Foundation
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We report a methodology for the catalytic asymmetric cross-coupling of two C(sp(3))-H bonds employing visible light as an economical and environmentally benign source of energy. Photoredox catalysis is used for the oxidation of a diarylmethane to the corresponding cation, which is then trapped by an enamine intermediate generated in situ from an aldehyde reactant and a secondary amine organocatalyst. Notably, this mild method is an ideal synthetic approach from the green chemistry point of view. It does not require preinstallation of functional groups, thereby constituting an atom economical, efficient transformation, and it allows the formation of a C-C bond with simultaneous installation of one or two new stereocenters in a highly enantio- and diastereoselective manner. Mechanistic studies by experimental and computational methods aid to clarify the origin of the observed enantioselectivity.
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