An improved C-P cross-coupling route for the synthesis of novel V-shaped aryldiphosphonic acids

  1. Stephen J. I. ShearanORCID Logo,
  2. Enrico Andreoli and
  3. Marco TaddeiORCID Logo

Submitting author affiliation: University of Pisa, Pisa, Italy

Beilstein Arch. 2022, 202259. https://doi.org/10.3762/bxiv.2022.59.v1

Published 05 Jul 2022

  • Preprint

Abstract

The synthesis of phosphonate esters is a topic of interest for various fields, including the preparation of phosphonic acids to be employed as organic linkers for the construction of metal phosphonate materials. Various methods have been reported to obtain phosphonate esters in the literature. Discussed here is the transition metal-catalysed cross-coupling reaction, often referred to as the Tavs reaction, which employs NiCl2 as a pre-catalyst in the phosphonylation of aryl bromide substrates using triisopropyl phosphite. We report an improvement to the existing method which decreases the reaction time from 24+ hours to around 4 hours, with yields above 80%. Compared to conventional methods, our procedure requires no solvent and involves a different order of addition of reactants. This new method was employed in the synthesis of three novel aryl phosphonate esters which were subsequently transformed to phosphonic acids through silylation and hydrolysis.

Keywords: Cross-coupling reaction; transition metal catalysis; phosphonate esters; arylphosphonic acids

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Shearan, S. J. I.; Andreoli, E.; Taddei, M. Beilstein Arch. 2022, 202259. doi:10.3762/bxiv.2022.59.v1

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