Chemo-, regio- and stereoselective synthesis of (E)-γ,γ-diarylvinylphosphonates from α-hydroxyallylphosphonates in TFA

Abstract

We report a mild and efficient protocol for the synthesis of γ,γ-diarylvinylphosphonates via dehydrative γ-selective arylation of α-hydroxyallylphosphonates. The reaction of α-hydroxyallylphosphonates with phenols proceeds smoothly in the presence of trifluoroacetic acid (TFA) to give the desired γ-arylation products. This method enables a straightforward synthesis of γ,γ-diarylvinylphosphonates from readily available α-hydroxyallylphosphonates under mild reaction conditions. DFT calculations provide mechanistic insights into the reaction pathways.