A New Route to Water-Soluble Sulfonated Phosphines

Abstract

Among the water-soluble phosphines sulfonated arylphosphines have been widely studied, particularly in the field of organometallic chemistry and biphasic catalysis because such ligands accord water-solubility to coordination compounds and thus afford means to separate easily the organic components from the catalysts in the aqucous phase ^1–3. More recently, mono- and tri-sulfonated triphenylphosphine have found applications in organic synthesis for the preparation of specifically deuterated alkenes and more generally for nucleophilic additions in water^4–8. Sulfonated triarylphosphines or alkyldiarylphosphines have been prepared by sulfonation with oleum of the corresponding phosphines on one or several aromatic nuclei^9–11. The sulfonation leads usually to mixtures of compounds having various degrees of sulfonation and to oxidation at phosphorus which forces subsequent separations^11–12. On the other hand this direct sulfonation method is not convenient for the synthesis of hydrophilic phosphines bearing functionalities on alkyl chains.