Metal‐Free Visible‐Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism
Dan Louvel, Aida Chelagha, Jean Rouillon, Pierre‐Adrien Payard, Lhoussain Khrouz, Cyrille Monnereau, Anis Tlili
Abstract
Abstract The first metal‐free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo‐photoredox conditions, aryl diazonium salts react with a readily available SO 2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron‐rich and ‐poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.
Topics & Concepts
NucleophileChemistryElectron paramagnetic resonanceArylPhotochemistryCombinatorial chemistryMetalFunctional groupPhotoredox catalysisReaction mechanismOrganic chemistryCatalysisPhotocatalysisPhysicsNuclear magnetic resonanceAlkylPolymerSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsFluorine in Organic Chemistry