A Highly Effective Pd/Cu-Catalyzed Coupling Reaction of Terminal Alkynes with Organic Halides Promoted by Tetrabutylammonium Fluoride or Hydroxide

All articles of this category Coupling reaction of terminal alkynes catalyzed by Pd/Cu with several organic electrophiles is shown to proceed by use of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide (TBAOH) as an activator. Treatment of 1-octyne and 4-methoxy-iodobenzene in the presence of 2.0 equiv of TBAOH, 1 mol% of PdCl 2 (PPh 3 ) 3 , and 2 mol% of CuI affords 1-phenyl-1-octyne in 98% yield after stirring at room temperature for 1 h. The new coupling reaction is also applied to polymer synthesis via polycondensation of a diyne and a diiodoarene. Sonogashira-Hagihara coupling - Pd/Cu catalyst - terminal alkynes - tetrabutylammonium fluoride - tetrabutylammonium hydroxide - polycondensation