Chemo-, regio- and stereoselective synthesis of (E)-γ,γ-diarylvinylphosphonates from α-hydroxyallylphosphonates in
Babak Kaboudin1, Abolfazl Yadghybi1, Hikaru Yanai2
1Department of Chemistry, Institute for Advanced Studies in Basic Sciences, Gava Zang, Zanjan, Iran. kaboudin@iasbs.ac.ir.
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.
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