Phase transfer Pd(O) catalyzed polymerization reactions. I. Synthesis of 1,2‐(4,4′;‐dialkoxyaryl) acetylene monomers and 1,4‐Bis[2‐(4′,4″‐dialkoxyphenyl)ethynyl]benzene derivatives by phase transfer Pd(O)/Cu(I) catalyzed coupling reactions

Several 1,2‐(4,4'‐dialkoxyaryl)acetylene monomers containing similar or dissimilar substituents were prepared by one of three variations of a one pot phase transfer Pd(O)/Cu(I) catalyzed coupling of aryl halides with a protected acetylene. The three steps within a single flask involved first coupling of the appropriate 1‐halo‐4‐alkoxybenzene derivative with 2‐methyl‐3‐butyn‐2‐ol, followed by cleavage of the carbinol group to form an aryl acetylide, and finally a second coupling of an aryl halide with the aryl acetylide. Best results were obtained when elevated temperatures and solid‐liquid phase transfer reaction conditions were used. Some 1,4‐bis[2‐(4',4”‐dialkoxyphenyl)ethynyl]benzene compounds were also prepared.