Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system

Beilstein J Org Chem. 2013 Oct 23:9:2189-93. doi: 10.3762/bjoc.9.257. eCollection 2013.

Abstract

Regioselective conjugate 1,4-trifluoromethylation of α,β-unsaturated ketones by the use of shelf-stable electrophilic trifluoromethylating reagents, S-(trifluoromethyl)diphenylsulfonium salts and copper under mild conditions is described. A wide range of acyclic aryl-aryl-enones and aryl-alkyl-enones were converted into β-trifluoromethylated ketones in low to moderate yields.

Keywords: 1,4-addition; Michael addition; copper; fluorine; organo-fluorine; trifluoromethylation.