Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes
Yang Liu, Simone Battaglioli, Lorenzo Lombardi, Arianna Menichetti, Giovanni Valenti, Marco Montalti, Marco Bandini
Abstract
The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.
Topics & Concepts
Allylic rearrangementChemistryRegioselectivitySurface modificationIntramolecular forceIntermolecular forceStoichiometryCatalysisPhotoredox catalysisCombinatorial chemistryPhotochemistryMoleculeOrganic chemistryPhotocatalysisPhysical chemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques