Asymmetric C–H Dehydrogenative Allylic Alkylation by Ternary Photoredox-Cobalt-Chiral Primary Amine Catalysis under Visible Light
Zongbin Jia, Long Zhang, Sanzhong Luo
Abstract
We report herein an asymmetric C-H dehydrogenative allylic alkylation by a synergistic catalytic system involving a chiral primary amine, a photoredox catalyst, and a cobaloxime cocatalyst. The ternary catalytic system enables the coupling of β-ketocarbonyls and olefins with good yields and high enantioselectivities. Mechanism studies disclosed a cooperative radical addition process with a chiral α-imino radical and Co(II)-metalloradical wherein the chiral primary aminocatalyst and the cobaloxime catalyst work in concert to control the stereoinduction.
Topics & Concepts
ChemistryCatalysisPrimary (astronomy)AlkylationTernary operationAmine gas treatingPhotoredox catalysisTsuji–Trost reactionAllylic rearrangementCobaltCombinatorial chemistryMedicinal chemistryPhotochemistryOrganic chemistryPhotocatalysisComputer scienceAstronomyProgramming languagePhysicsCatalytic C–H Functionalization MethodsCO2 Reduction Techniques and CatalystsRadical Photochemical Reactions