PHASE-TRANSFER PD(O) CATALYZED POLYMERIZATION REACTIONS .1. 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. Copyright © 1990 John Wiley & Sons, Inc.