Novel Preparation of Ion-supported Triphenylphosphines and Their Synthetic Utility

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Novel ion-supported Ph3P compounds, 4-(diphenylphosphino)-benzyltrimethylammonium bromide (A) and N-methyl-N-[4-(diphenylphosphino) -benzyl]pyrrolidinium bromide (B), were prepared, and they were used for the esterification of carboxylic acid with the Mitsunobu reaction, and the Wittig reaction as a stoichiometoric reagent, and the Mizoroki-Heck reaction and the Sonogashira reaction for ligand with Pd. The advantages of using these ion-supported Ph_3P A and B are the simple isolation of the products by ether extraction due to their poor solubility in ether, and the easy recovery of the co-product, ion-supported Ph_3PO, by filtration in high yields (>90%), which could be regenerated and reused for the same reactions.