Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation

Dong Wang; C Grace Carlton; Masanori Tayu; Joseph J W McDouall; Gregory J P Perry; David J Procter

doi:10.1002/anie.202005531

Trifluoromethyl Sulfoxides: Reagents for Metal-Free C-H Trifluoromethylthiolation

Angew Chem Int Ed Engl. 2020 Sep 7;59(37):15918-15922. doi: 10.1002/anie.202005531. Epub 2020 Jul 15.

Authors

Dong Wang¹, C Grace Carlton¹, Masanori Tayu^{1

2}, Joseph J W McDouall¹, Gregory J P Perry¹, David J Procter¹

Affiliations

¹ Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
² Department of Chemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan.

Abstract

Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C-H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism.

Keywords: Pummerer reaction; arenes; reaction mechanisms; sulfoxides; trifluoromethylthiolation.