VINYLPHOSPHONIUM SALTS - STEREOSELECTIVE PALLADIUM-CATALYZED VINYLATION OF TRIPHENYLPHOSPHINE WITH VINYL TRIFLATES

The reaction of vinyl triflates with a slight excess of triphenylphosphine and 1-3 mol % Pd(PPh3)4 in refluxing THF results in the formation of the corresponding vinyltriphenylphosphonium triflate salts in good yield. A wide variety of salts, including cyclic ones, can be prepared. Unlike past syntheses of these compounds, pure stereoisomeric starting triflates stereoselectively yield stereoisomeric products. The current synthesis is especially useful for the preparation of Z isomers. © 1990, American Chemical Society. All rights reserved.