Identification and characterization of a new family of catalytically highly active imidazolin-2-ylidenes

Xinjun Luan, Ronaldo Mariz, Michele Gatti, Chiara Costabile, Albert Poater, Luigi Cavallo, Anthony Linden, Reto Dorta*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

98 Scopus citations

Abstract

A new class of easily accessible and stable imidazolin-2-ylidenes has been synthesized where the side chains are comprised of substituted naphthyl units. Introduction of the naphthyl groups generates C2-symmetric (rac) and Cs-symmetric (meso) atropisomers, and interconversion between the isomers is studied in detail both experimentally and computationally. Complete characterization of the carbenes includes rare examples of crystallographically characterized saturated NHC structures. Steric properties of the ligands and an investigation of their stability are also presented. In catalysis, the new ligands show versatility comparable to the most widely used NHCs IMes/SIMes or IPr/SIPr. Excellent catalytic results are obtained when either the NHC salts (ring-opening alkylation of epoxides), NHC-modified palladium compounds (C-C and C-N cross-couplings), or NHC-ruthenium complexes (ring-closing metathesis, RCM) are employed. In several cases, this new ligand family provides catalytic systems of higher reactivity than that observed with previously reported NHC compounds.

Original languageEnglish (US)
Pages (from-to)6848-6858
Number of pages11
JournalJournal of the American Chemical Society
Volume130
Issue number21
DOIs
StatePublished - May 28 2008

ASJC Scopus subject areas

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

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