A highly effective Pd/Cu-catalyzed coupling reaction of terminal alkynes with organic halides promoted by tetrabutylammonium fluoride or hydroxide

Coupling reaction of terminal alkynes catalyzed by Pd/ Cu with several orga nic electrophiles is shown to proceed by use of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide(TBAOH) as an activator. Treatment o f l-octyne and 4-methoxy-iodobenzene in the presence of 2.0 equiv of TBAOH, 1 mol% of PdCl2(PPh3)(3), and 2 mol% of Cul affords: 1-phenyl-1-octyne in 98% yield after stirring at room temperature for 1 h. The new coupling reac tion is also applied to polymer synthesis via polycondensation of a diyne a nd a diiodoarene.