One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols

Petrakis N. Chalikidi*, Taimuraz T. Magkoev, Andrey V. Gutnov, Oleg P. Demidov, Maxim G. Uchuskin*, Igor V. Trushkov and Vladimir T. Abaev

*North-Ossetian State University, Vatutina st. 46, Vladikavkaz, 362025; North-Ossetian State University, Vatutina st. 46, Vladikavkaz, 362025, Russia, Email: chalikidigmail.com, mupsu.ru

P. N. Chalkiki, T. T. Magkoev, A. V. Gutnov, O. P. Demidov, M. G. Uchuskin, I. V. Trushkov, V. T. Abaev, J. Org. Chem., 2021, 86, 9838-9846.

DOI: 10.1021/acs.joc.1c00733

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Abstract

Two approaches for the synthesis of substituted phosphonium salts from benzyl alcohols have been developed: direct mixing of alcohol, TMSBr, and PPh₃ in 1,4-dioxane followed by heating at 80 °C enables the conversion of acid-sensitive substrates, while sequential addition of TMSBr, and PPh₃ gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.

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Key Words

phosphonium salts

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ID: J42-Y2021