Iron diazoalkane chemistry: N-N bond hydrogenation and intramolecular C-H activation

Suzanne C. Bart, Amanda C. Bowman, Emil Lobkovsky, Paul J. Chirik

Research output: Contribution to journalArticle

75 Scopus citations

Abstract

Treatment of the intermediate spin ferrous bis(dinitrogen) complex, (iPrPDI)Fe(N2)2 (iPrPDI = 2,6-(2,6-iPr2-C6H3NCMe2)2C6H3N), with 1 equiv of N2CHSiMe3 afforded the corresponding iron diazoalkane compound, (iPrPDI)Fe(N2CHSiMe3). Spectroscopic studies in conjunction with the metrical parameters from the solid-state structure support an intermediate spin ferrous complex with a doubly reduced chelate and a neutral diazoalkane ligand. In solution at 23 °C, (iPrPDI)Fe(N2CHSiMe3) promotes the intramolecular C-H activation of an isopropyl aryl substituent with loss of SiMe4. Exposure of (iPrPDI)Fe(N2CHSiMe3) to 1 atm of H2 resulted in hydrogenative cleavage of the N-N and N-C bonds to yield (iPrPDI)Fe(NH3) and SiMe4. Similar N-N bond cleavage chemistry was observed upon addition of hydrazine to (iPrPDI)Fe(N2)2.

Original languageEnglish (US)
Pages (from-to)7212-7213
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number23
DOIs
StatePublished - Jun 13 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

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

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