Preparation of carboxylic arylphosphines by hydrolysis of the trifluoromethyl group

Daniel Herrera, Daniel Peral, J. Carles Bayón*

*Autor correspondiente de este trabajo

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Resumen

Triarylphosphines substituted with carboxylic and trifluoromethlyl groups have been prepared by the hydrolysis of trifluoromethyl groups using fuming sulfuric acid and boric acid. The reaction has been studied in a set of homoleptic and heteroleptic trifluoromethylated triarylphosphines and offers a new synthetic procedure for the preparation of carboxylic phosphines with a relatively simple methodology. The degree of carboxylation is modulated by the reaction conditions and is sensitive to the substitution pattern of the starting trifluoromethylated phosphines. A pH-dependent procedure based on the amphiphilic character of these phosphines was developed for their separation and purification. The electronic properties of the synthesized carboxylic-trifluoromethylated phosphines have been analyzed by 31P NMR of the corresponding selenide derivatives. Finally, the structures of two palladium complexes, containing the para and meta carboxylic-trifluoromethylated phosphines are also described, showing different dimeric structures.

Idioma originalInglés
Páginas (desde-hasta)7103-7114
Número de páginas12
PublicaciónRSC ADVANCES
Volumen12
N.º12
DOI
EstadoPublicada - 2 mar 2022

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