Synthesis of Bis(2,2,2-Trifluoroethyl) (Z)-Vinylphosphonates

Abstract

A new method for the synthesis of bis (2,2,2- trifluoroethyl) (Z)-vinyl phosphonates from bis (2,2,2-trifluoroethyl) 1-alkynyl phosphonates is described. 1-Alkynyl phosphonates, in the presence of Lindlar's catalyst, trifluoroethanol and H2 (g), are used to prepare the corresponding vinylphosphonates via a semireductive synthetic approach. With the starting materials in hand, specifically the 1-alkynylphophonates, which were synthesized using bis(2,2,2-trifluoroethyl)phosphorochloridate and the commercially available 1-alkynes, the obtaining of the desired target was accomplished. The semireduction of the triple bond was successful using Lindlar's catalyst in the presence of quinoline with 2,2,2-trifluoroethanol as reaction solvent. Additionally, a modified approach to this synthesis is explored such that only the kinetic (Z) isomer is formed.