Preparation of carboxylic arylphosphines by hydrolysis of the trifluoromethyl group. Issue 12 (2nd March 2022)

• Record Type: Journal Article
• Authors: Herrera, Daniel; Peral, Daniel; Bayón, J. Carles
• Is Part Of: RSC advances. Volume 12:Issue 12(2022)
• Page Start: 7103
• Page End: 7114
• Publication Date: 2022-03-02
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra00420h
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Preparation of carboxylic triarylphosphines by hydrolysis of the trifluoromethyl group in acid media. Abstract : 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 31 P 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.