N-H versus C-H activation of a pyrrole imine at {Cp*Ir}: A computational and experimental study

David L. Davies, S. M A Donald, Omar Al-Duaij, John Fawcett, Craig Little, Stuart A. Macgregor

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

Reaction of a pyrrole imine with [IrCl2Cp*] 2/NaOAc leads to N-H activation in preference to C - H activation at the pyrrole; however, with the N-methylated ligand C-H activation occurs. Density functional calculations show that N-H bond activation is both kinetically and thermodynamically preferred to C-H activation. Both reactions occur with relatively low energy barriers by an electrophilic agostic interaction with the metal with simultaneous intramolecular hydrogen bonding with acetate leading to deprotonation via a six-membered transition state. © 2006 American Chemical Society.

Original languageEnglish
Pages (from-to)5976-5978
Number of pages3
JournalOrganometallics
Volume25
Issue number26
DOIs
Publication statusPublished - 18 Dec 2006

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