Stereoselective preparation of (E)- and (Z)-alpha-fluorostilbenes via palladium-catalyzed cross-coupling reaction of high E/Z ratio and (Z)-1-bromo-1-fluoroalkenes

A highly stereoselective method to prepare both (E)- and (Z)-alpha-fluorostilbenes is described. 1-Bromo-1-fluoroalkenes (E/Z approximately 1:1), a readily available starting material, isomerizes to high E/Z ratios by storage at -20 degrees C or by photolysis at 254 nm. Stille coupling between these high E/Z 1-bromo-1-fluoroalkenes and aryl stannanes gave (Z)-alpha-fluorostilbenes in high stereoselectivity. (Z)-1-Bromo-1-fluoroalkenes, which were kinetically separated from 1-bromo-1-fluoroalkenes (E/Z approximately 1:1), can participate in Suzuki coupling reactions to give (E)-alpha-fluorostilbenes stereoselectively.