Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes

Lvqi Jiang; Tianqi Ding; Wen-Bin Yi; Xin Zeng; Wei Zhang

doi:10.1021/acs.orglett.8b00581

Fluoroalkylsulfonyl Chlorides Promoted Vicinal Chloro-fluoroalkylthiolation of Alkenes and Alkynes

Org Lett. 2018 Apr 20;20(8):2236-2240. doi: 10.1021/acs.orglett.8b00581. Epub 2018 Apr 6.

Authors

Lvqi Jiang¹, Tianqi Ding¹, Wen-Bin Yi¹, Xin Zeng¹, Wei Zhang²

Affiliations

¹ School of Chemical Engineering , Nanjing University of Science and Technology , Nanjing 210094 , P. R. China.
² Centre for Green Chemistry and Department of Chemistry , University of Massachusetts Boston , 100 Morrissey Boulevard , Boston , Massachusetts 02125 , United States.

PMID: 29624070
DOI: 10.1021/acs.orglett.8b00581

Abstract

The unprecedented use of CF₃SO₂Cl for direct bifunctional chloro-trifluoromethylthiolation of alkenes and alkynes is reported. CF₃SCl, which is generated by the reduction of PPh₃, undergoes electrophilic addition and then chlorination to give the bifunctionalized products without using an additional chlorine source. The method is also applicable for chloro-difluoromethylthiolation using CF₂HSO₂Cl.

Publication types

Research Support, Non-U.S. Gov't