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Highly Regio- and Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis

Yan-Lin Li, Shiqi Zhang, Jie Chen, Ji‐Bao Xia

2021Journal of the American Chemical Society160 citationsDOI

Abstract

A Co-catalyzed highly regio- and enantioselective reductive coupling of alkynes and aldehydes has been developed under visible light photoredox dual catalysis. A variety of enantioenriched allylic alcohols have been obtained by using unsymmetrical internal alkynes and commercially available catalyst, chiral ligand, and reagents. It is noteworthy that this approach has considerable advantages, such as excellent regio- (>95:5 for >40 examples), stereo- (up to >95:5 E/Z), and enantioselectivity (92–99% ee, >35 examples) control, mild reaction conditions, broad substrate scope, and good functional group compatibility, making it a great improvement to enantioselective alkyne–aldehyde reductive coupling reactions.

Topics & Concepts

ChemistryEnantioselective synthesisCobaltCatalysisCombinatorial chemistryDual (grammatical number)Coupling (piping)Photoredox catalysisOrganic chemistryPhotocatalysisArtMechanical engineeringLiteratureEngineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques
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