Two phenyl rings of triphenylphosphane have been modified by electron-withdrawing trifluoromethyl groups. A methoxy group has been introduced at the para-position of the third ring. Due to the activating effect of the methoxy group, the phosphane can be monosulfonated under mild conditions and with complete selectivity. The novel ligand, sodium 5-[bis-(4-trifluoromethylphenyl)phosphanyl]-2-methoxybenzenesulfonate, has been obtained in quantitative yield, and it has an outstanding π-acceptor capacity among the known sulfonated triarylphosphanes. It is not soluble in water but soluble in light alcohols and ionic liquids. Its solubility properties allow facile catalyst separation without water.
Facile Synthesis of a Monosulfonated Triphenylphosphane (TPPMS) Derived Ligand having Strong π-Acceptor Character
Adv. Synth. Catal. 2006, 348, 1306-1310.