Novel synthesis of (Z)-difluoroacrylates via a highly stereoselective addition-elimination reaction

Org Lett. 2006 Mar 2;8(5):843-5. doi: 10.1021/ol052897g.

Abstract

On treating readily prepared benzyl 2,3,3-trifluoroacrylate with various Grignard reagents, e.g., aryl-, alkyl-, or alkenylmagnesium halide, in the presence of a catalytic amount of copper(I) salt in THF at -78 degrees C for 1 h, the corresponding alpha,beta-difluoroacrylates were obtained in 54-98% yields with high Z-selectivity.