Iron-catalyzed [2π + 2π] cycloaddition of α,ω-dienes: The importance of redox-active supporting ligands

Marco W. Bouwkamp, Amanda C. Bowman, Emil Lobkovsky, Paul J. Chirik

Research output: Contribution to journalArticlepeer-review

243 Scopus citations

Abstract

The bis(imino)pyridine iron bis(dinitrogen) complex, ( i PrPDI)Fe(N 2 ) 2 ( i PrPDI = 2,6-(2,6- i Pr 2 C 6 H 3 NCR) 2 C 5 H 3 N), serves as an efficient precursor for the catalytic [2π + 2π] cycloaddition of α,ω-dienes to yield the corresponding bicycles. For amine substrates, the rate of catalytic turnover increases with the size of the nitrogen substituents, demonstrating competing heterocycle coordination and product inhibition. In one case, a bis(imino)pyridine iron azobicycloheptane product was characterized by X-ray diffraction. Preliminary mechanistic studies highlight the importance of the redox activity of the bis(imino)pyridine ligand to maintain the ferrous oxidation state throughout the catalytic cycle.

Original languageEnglish (US)
Pages (from-to)13340-13341
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number41
DOIs
StatePublished - Oct 18 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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