Reductive Cross-Coupling of Olefins via a Radical Pathway
Wei Zhou, Igor A. Dmitriev, Paolo Melchiorre
Abstract
High Resolution Image Download MS PowerPoint Slide Olefins are widely available at low costs, which explains the usefulness of developing new methods for their functionalization. Here we report a simple protocol that uses a photoredox catalyst and an inexpensive thiol catalyst to stitch together two olefins, forming a new C–C bond. Specifically, an electron-poor olefin is reduced by the photoredox catalyst to generate, upon protonation, a carbon radical, which is then captured by a neutral olefin. This intermolecular cross-coupling process provides a tool for rapidly synthesizing sp 3 -dense molecules from olefins using an unconventional disconnection.
Topics & Concepts
ChemistryOlefin fiberIntermolecular forceProtonationCatalysisPhotoredox catalysisPhotochemistryCoupling (piping)Surface modificationMoleculeCombinatorial chemistryOrganic chemistryPhysical chemistryEngineeringIonPhotocatalysisMechanical engineeringRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques