Transition metal-free trifluoromethylation of n-Allylamides with sodium Trifluoromethanesulfinate: Synthesis of Trifluoromethyl-containing oxazolines

Abstract

A transition metal-free method for the trifluoromethylation of N-allylamides has been developed, and the corresponding trifluoromethylcontaining oxazolines were prepared in moderate to good yields. The protocol uses readily available substituted N-allylamides as the starting materials, inexpensive and easily stored sodium trifluoro- ACHTUNGTRENUNGmethanesulfinate as the trifluoromethyl source, iodobenzene diacetate as the oxidant, and the procedure involves sequential intermolecular trifluoromethylation of alkenes with sodium trifluoro- ACHTUNGTRENUNGmethanesulfinate and intramolecular cyclization. This is the first example to prepare CF3-containing oxazolines. Therefore, the present method should afford an efficient and practical strategy for synthesis of other CF3-containing cyclic compounds.