Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
Mario Leypold, Kyan A. D’Angelo, Mohammad Movassaghi
Abstract
The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies identified activated sulfoxides as promoters of the desired transformation and enabled the extension of the methodology from benzylic to aliphatic amide substrates.
Topics & Concepts
SulfidationChemistryReagentSulfoniumAmideElectrophileSulfoxideSulfideCombinatorial chemistryOrganic chemistryCatalysisSalt (chemistry)Advanced Synthetic Organic ChemistrySulfur-Based Synthesis TechniquesChemical synthesis and alkaloids