Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water

• DOI: 10.1021/acs.joc.6b01549
• Publication Date: 2016-10-19T18:42:41Z
• Authors: Chao Wu; Panpan Yang; Zhimin Fu; Yong Peng; Xin Wang; Zuozhi Zhang; Fang Liu; Wenyi Li; Zhizhang Li; Weimin He
• Keywords: Sulfonyl; Sulfinic acid; Alkyne

We report the atom-economic and environmentally friendly synthesis of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds in water. The mechanism study reveals that hydrosulfonylation alkynylcarbonyl with sulfinic acids proceeds via a features acid molecule protonating an alkynyl motif to form ethenium intermediate, which subsequently reacted sulfonyl anion afford desired products. intermediate differentiated electronic steric demands between two substituents on C≡C triple bond alkyne substrates exhibit high regio- stereoselectivity from wide range compounds.