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Updated: Jun 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
Tetraarylphosphonium salts as soluble supports for oxidative catalysts and reagents
Marie-Noelle Roy1, Jean-Christophe Poupon, André B Charette
1Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Abstract:
Tetraarylphosphonium (TAP)-supported DMSO, TEMPO, and DIB reagents were synthesized and used for the oxidation of alcohols, including Swern oxidation and for the alpha-acetoxylation of ketones. By taking advantage of the predictable solubility properties of the TAP unit, simple precipitation and filtration of the phosphonium moiety permit complete separation of the desired oxidation products. This paper describes the preparation of these three TAP-supported oxidative reagents and their activity in the aforementioned oxidative transformations. Furthermore, we have demonstrated that these reagents can be recycled directly when used in catalytic processes and following regeneration when used in stoichiometric processes.
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