Tandem alkylation defluorination reaction: Synthesis of 2-(N-alkyl-N-aryl)amino-3,3-difluoropropenoates from 2-(N-aryl)imino-3,3,3-trifluoropropanoates

A novel synthesis of fluoroolefins from trifluoromethylated compounds with organometallic reagents was developed The reaction seems to proceed via 1,4-alkylation on imino nitrogen followed by defluorination of the trifluoromethyl group. Diethylzinc was found to be an efficient reagent for the preparation of 2-(N-aryl-N-ethyl)amino-3,3-difluoropropenoates in excellent yield A similar synthesis of monofluoroolefin with Grignard reagent was also developed.