One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols
2021
Chalikidi, Petrakis N. | Magkoev, Taimuraz T. | Gutnov, Andrey V. | Demidov, Oleg P. | Uchuskin, Maxim G. | Trushkov, Igor V. | Abaev, Vladimir T.
Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.
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