Visible-Light-Mediated Intermolecular Radical Conjugate Addition for the Construction of Vicinal Quaternary Carbon Centers
Lei Li, Lili Fang, Wei-Ping Wu, Jin Zhu
Abstract
The visible light-driven organophotoredox catalysis is reported for the construction of vicinal quaternary carbon centers. Intermolecular conjugate addition of alkyl radicals, derived from 2,2-disubstituted dihydroquinazolinones, to Michael acceptors under blue light irradiation and rhodamine B catalysis allows the facile assembly of diverse, vicinal secondary/quaternary, tertiary/quaternary, and quaternary/quaternary carbon centers at room temperature. Our method provides a synthetically versatile protocol since both 2,2-disubstituted dihydroquinazolinones and Michael acceptors can be conveniently prepared from readily available ketones.
Topics & Concepts
VicinalChemistryConjugateQuaternary carbonCatalysisPhotochemistryIntermolecular forceAlkylQuaternaryMichael reactionCombinatorial chemistryMoleculeOrganic chemistryEnantioselective synthesisPaleontologyMathematical analysisMathematicsBiologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques