Transition-Metal-Free Direct Trifluoromethylthiolation and Trifluoromethylsulfoxidation of Electron-Rich Aromatics with CF3SO2Na in the Presence of PCl3

Xia Zhao; Aoqi Wei; Bo Yang; Tianjiao Li; Quan Li; Di Qiu; Kui Lu

doi:10.1021/acs.joc.7b01226

Transition-Metal-Free Direct Trifluoromethylthiolation and Trifluoromethylsulfoxidation of Electron-Rich Aromatics with CF₃SO₂Na in the Presence of PCl₃

J Org Chem. 2017 Sep 1;82(17):9175-9181. doi: 10.1021/acs.joc.7b01226. Epub 2017 Aug 23.

Authors

Xia Zhao¹, Aoqi Wei¹, Bo Yang¹, Tianjiao Li¹, Quan Li², Di Qiu¹, Kui Lu²

Affiliations

¹ College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University , Tianjin 300387, China.
² College of Biotechnology, Tianjin University of Science & Technology , Tianjin 300457, China.

PMID: 28809561
DOI: 10.1021/acs.joc.7b01226

Abstract

A new transition-metal-free route for the direct trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics with CF₃SO₂Na in the presence of PCl₃ was developed. Notably, PCl₃ was used as a reducing and chlorination reagent. The transition-metal-free protocol utilized cheap and readily available reagents and exhibited good atom economy; therefore, it will serve as an alternative and practical strategy for the trifluoromethylthiolation and trifluoromethylsulfoxidation of electron-rich aromatics.

Publication types

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