Synthesis of Vinyl and 1,3‐Dienyl Sulfones Enabled by Photochemical Excitation of Halogen‐Bonding Complexes
Helena F. Piedra, Carlos Valdés, Manuel Plaza
Abstract
Abstract The photochemical catalyst‐free radical‐based synthesis of vinyl and 1,3‐dienyl sulfones is disclosed. Mechanistic investigations support that the transformations rely on a visible‐light‐promoted activation of a halogen‐bonding complex, which is formed between an alkenyl (or 1,3‐dienyl) bromide and a sodium sulfinate salt. The reactions exhibit a wide functional group tolerance (compatible with heteroatoms, electron‐withdrawing and electron‐donating groups), finding application in the structural modification of biologically relevant molecules. Eventually, a continuous flow protocol was developed to upscale these transformations.
Topics & Concepts
ChemistryHeteroatomHalogenHalogen bondBromideFunctional groupPhotochemistryVinyl bromideMoleculeCatalysisCombinatorial chemistryPolymer chemistryOrganic chemistryAlkylPolymerSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods