Bulky N-heterocyclic carbene IPr* in selected organo- and transition metal-mediated catalytic applications

János Balogh, Alexandra M.Z. Slawin, Steven P. Nolan

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Abstract

A series of studies were conducted to probe the stability and reactivity of a very sterically encumbered N-heterocyclic carbene. The X-ray structure of the NHC IPr* (IPr* = 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl) imidazol-2-ylidene) was determined. IPr* was used as an organocatalyst in transesterification reactions. Steric and electronic parameters characterizing IPr* were determined via the synthesis of a nickel-carbonyl complex, [Ni(CO) 3(IPr*)]. A related complex, [(Cp*)Ru(IPr*) Cl] (Cp* = η 5-C 5Me 5), was prepared and characterized by X-ray crystallography, and its catalytic performance in the racemization of chiral alcohols is reported. The catalytic performance of the NHC and of its transition metal derivatives permit establishing the standing of this uniquely bulky member among the NHC family.

Original languageEnglish
Pages (from-to)3259-3263
Number of pages5
JournalOrganometallics
Volume31
Issue number8
DOIs
Publication statusPublished - 23 Apr 2012

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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