Copper-Catalyzed Asymmetric Cyanation of Alkenes via Carbonyl-Assisted Coupling of Alkyl-Substituted Carbon-Centered Radicals
Song Zhou, Guoyu Zhang, Liang Fu, Pinhong Chen, Yibiao Li, Guosheng Liu
Abstract
Based on a copper-catalyzed radical relay strategy, the first copper-catalyzed asymmetric cyanation of alkyl-substituted alkenes has been developed. The reaction, featuring mild reaction conditions and excellent functional group compatibilities, provides an easy access to a wide array of structurally diverse enantioenriched alkyl nitriles in good yields. Notably, an unstable carbon-centered radical generated by trifluoromethyl radical addition across terminal alkenes can be enantioselectively trapped by chiral L*Cu(CN)2 with the assistance of a carbonyl group.
Topics & Concepts
CyanationChemistryAlkylCatalysisRadicalTrifluoromethylCopperCarbon fibersCombinatorial chemistryMedicinal chemistryPhotochemistryOrganic chemistryMaterials scienceComposite materialComposite numberCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques