Platinum stilbazoles: Ring-walking coupled with aryl-halide bond activation

David Strawser, Amir Karton, Olena V. Zenkina, Mark A. Iron, Linda J.W. Shimon, Jan M.L. Martin, Milko E. Van Der Boom

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Abstract

The reaction between tetrakis(triethylphosphine)platinum(0) and 4-[trans-2-(4-bromophenyl)vinyl]pyridine (1) is examined. Initially, the metal center coordinates to the bridging double bond of 1. Complexes 2 and 3 were fully characterized, and their X-ray crystallography structures are presented. Upon heating, either in solution or in the solid state, complex 2 undergoes C-Br oxidative addition to give complex 3. Kinetic studies revealed that this conversion is unimolecular and does not involve dissociation of the metal center from the double bond. Density functional studies show that a plausible mechanism involves the metal center "walking" around the π-system from the bridging C=C double bond to the C-Br bond.

Original languageEnglish
Pages (from-to)9322-9323
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number26
DOIs
Publication statusPublished - Jul 6 2005

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Strawser, D., Karton, A., Zenkina, O. V., Iron, M. A., Shimon, L. J. W., Martin, J. M. L., & Van Der Boom, M. E. (2005). Platinum stilbazoles: Ring-walking coupled with aryl-halide bond activation. Journal of the American Chemical Society, 127(26), 9322-9323. https://doi.org/10.1021/ja050613h