N-N bond cleavage in diazoalkanes by a Bis(imino)pyridine iron complex

Sarah K. Russell, Emil Lobkovsky, Paul J. Chirik

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52 Scopus citations


Addition of monosubstituted diazoalkanes, N 2CHR (R = Ph, p-Tolyl, tBu, Cy), to the bis(imino) pyridine iron dinitrogen complex, ( iPrPDI)Fe(N 2)2, at 23 °C in benzene-d 6 resulted in rapid cleavage of the N-N bond to yield the iron nitrile and imine complexes, ( iPrPDI)FeNCR and ( iPrPDI) FeHNCHR, respectively. Aryl azines were also cleaved with ( iPrPDI) Fe(N 2) 2 and yielded the same products. Mechanistic studies support a pathway involving initial formation of an iron alkylidene followed by rapid [4π + 2π] cycloaddition with another equivalent of diazoalkane. Subsequent rate-determining 1,3-hydrogen migration followed by retrocycloaddition yields the observed products.

Original languageEnglish (US)
Pages (from-to)36-37
Number of pages2
JournalJournal of the American Chemical Society
Issue number1
StatePublished - Jan 14 2009
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry


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