Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator
Fuyang Yue, Jianyang Dong, Yuxiu Liu, Qingmin Wang
Abstract
Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.
Topics & Concepts
ChemistryAlkylActivator (genetics)Lewis acids and basesBoronic acidCombinatorial chemistryOrganic chemistrySurface modificationCatalysisBiochemistryPhysical chemistryGeneRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods