Synthesis and characterization of low generation halogenated linear poly(arylpropargyl)ether (PAPE) branches via selective palladium catalyzed coupling reactions

A rapid convergent synthesis of first- and second-generation halogenated linear poly(arylpropargyl ether) branches 7 and 10 is described. The key step of the sequence studied involves a selective Sonogashira–Linstrumelle (S–L) cross-coupling reaction of aryl iodides with alkynes bearing an sp2-carbon–iodine bond. Application to the synthesis of functionalized first-generation poly(arylpropargylether) stars having a benzene-1,3,5-tricarboxylic acid core has been realized.