Metal‐Free Synthesis of (<i>E</i>)‐Vinyl Sulfones <i>via</i> An Insertion of Sulfur Dioxide/1,5‐Hydrogen Atom Transfer Sequence
Fu‐Sheng He, Yanfang Yao, Wenlin Xie, Jie Wu
Abstract
Abstract A metal‐free three‐component reaction of propargyl alcohols, sodium metabisulfite, and aryldiazonium tetrafluoroborates under mild conditions is described. The reaction proceeds efficiently at room temperature without the need of any catalysts, affording the corresponding ( E )‐vinyl sulfones in moderate to good yields with excellent functional group tolerance. Preliminary mechanistic studies show that a vinyl radical‐induced 1,5‐hydrogen atom transfer process and functional group migration are involved, resulting in the cleavage of inert C−H and C−C bonds in sequence. magnified image
Topics & Concepts
ChemistryPropargylHydrogen atomCatalysisMetalSulfurFunctional groupHydrogenPhotochemistryPolymer chemistryOrganic chemistryGroup (periodic table)PolymerSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods