Alkyne Reactions with Arylpalladium Compounds

W. Tao, L. J. Silverberg, A. L. Rheingold, R. F. Heck

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187 Scopus citations


Cyclopalladated N, N-dimethylbenzylamine trifluoromethanesulfonate reacts with diphenylacetylene to form a benzofulvene derivative, VIII. New complexes of two alkyne units with one cyclopalladated chloro dimer were prepared including a bis(dimethyl acetylenedicarboxylate)-cyclopalladated dimethylbenzylamine product and a 3-hexyne-cyclopalladated [(dimethylamino)methyl]ferrocene complex. Several 3:1 alkyne to aryl halide compounds have been formed catalytically from aryl iodides or bromides and alkynes. They are pentaalkylcyclopentadiene derivatives II. Methyl o-iodobenzoate with some alkynes yields isocoumarin derivatives. In some cases hexacyclic or tetracyclic 4:2 alkyne to aryl halide products are formed, also. Mechanisms are suggested to explain these and related reactions.

Original languageEnglish (US)
Pages (from-to)2550-2559
Number of pages10
Issue number11
StatePublished - Nov 1 1989

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


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