Zinc‐Mediated Intermolecular Reductive Radical Fluoroalkylsulfination of Unsaturated Carbon–Carbon Bonds with Fluoroalkyl Bromides and Sulfur Dioxide.

Liu, Yongan; Lin, Qiongzhen; Xiao, Zhiwei; Zheng, Changge; Guo, Yong; Chen, Qing‐Yun; Liu, Chao

A versatile and general zinc‐mediated intermolecular reductive radical fluoroalkylsulfination of unsaturated C−C bonds has been developed using readily available fluoroalkyl bromides and 1,4‐diazabicyclo[2.2.2]octane‐bis(sulfur dioxide) adduct (DABSO) with wide substrate scope and excellent functional group tolerance. Sulfur dioxide anion radical generated in situ from the reduction of sulfur dioxide with zinc may be involved in the reaction mechanism. A zinc‐mediated intermolecular reductive radical fluoroalkylsulfination of unsaturated C−C bonds has been developed using readily available fluoroalkyl bromides, 1,4‐diazabicyclo[2.2.2]octane‐bis(sulfur dioxide) adduct (DABSO) and N‐fluorobenzenesulfonimide (NFSI) with wide substrate scope and excellent functional group tolerance. Sulfur dioxide anion radical generated from the reduction of sulfur dioxide with zinc may be involved in the reaction mechanism.

INTERMOLECULAR interactions; CARBON-carbon bonds; BROMIDES; CHEMICAL adducts; SUBSTRATES (Materials science); FLUOROALKYL compounds; FUNCTIONAL groups; SULFUR dioxide

Chemistry - A European Journal, 2019, Vol 25, Issue 7, p1824

0947-6539

Academic Journal

10.1002/chem.201805526