Sulfur-Arylation of Sulfenamides via Chan–Lam Coupling with Boronic Acids: Access to High Oxidation State Sulfur Pharmacophores
Nathaniel S. Greenwood, Jonathan A. Ellman
Abstract
Sulfur-arylation of sulfenamides is reported. This reaction proceeds via a Chan-Lam-type coupling with commercially abundant boronic acids to give sulfilimines. A broad scope was established with a variety of readily accessible aryl and alkyl sulfenamide and boronic acid inputs. Synthetic utility and functional group compatibility were further demonstrated through the direct late-stage introduction of sulfilimines into approved drugs. Derivatization of the sulfilimine products provided access to medicinally relevant sulfoximines and sulfondiimines.
Topics & Concepts
ChemistrySulfenamideArylPharmacophoreBoronic acidCombinatorial chemistrySulfurDerivatizationAlkylFunctional groupOrganic chemistryStereochemistryHigh-performance liquid chromatographyNatural rubberVulcanizationPolymerSynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods