A Copper(I)‐Catalyzed Sulfonylative Hiyama Cross‐Coupling
Aurélien Adenot, Lucile Anthore‐Dalion, Emmanuel Nicolas, J.‐C. Berthet, P. Thuéry, Thibault Cantat
Abstract
Abstract An air‐tolerant Cu‐catalyzed sulfonylative Hiyama cross‐coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)‐sulfinate intermediate via fast insertion of a SO 2 molecule.
Topics & Concepts
SilanesArylChemistryCatalysisCopperCoupling reactionMoleculePolarFunctional groupCoupling (piping)Reaction mechanismMechanism (biology)Polymer chemistryCombinatorial chemistryComputational chemistryOrganic chemistryMaterials sciencePolymerSilaneAlkylMetallurgyAstronomyEpistemologyPhysicsPhilosophySulfur-Based Synthesis TechniquesCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods