Synthesis, X-ray structures, and catalytic activities of (kappa(2)-C,N)-palladacycles bearing imidazol-2-ylidenes

Gunay M. E., Gumusada R., Özdemir N., Dincer M., Cetinkaya B.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.694, no.15, pp.2343-2349, 2009 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 694 Issue: 15
  • Publication Date: 2009
  • Doi Number: 10.1016/j.jorganchem.2009.03.034
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.2343-2349
  • Keywords: Palladacycles, N-heterocyclic carbene, Imidazol-2-ylidenes, Suzuki-Miyaura coupling, N-HETEROCYCLIC CARBENES, SUZUKI-MIYAURA, EFFICIENT CATALYSTS, PALLADIUM COMPLEXES, PHENYLBORONIC ACID, COUPLING REACTIONS, CRYSTAL-STRUCTURE, LIGANDS, PALLADACYCLES, DEHALOGENATION
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

Quaternisation of methylimidazole (1) by methyl substituted benzyl bromides afforded imidazolium salts (2) which were converted to (kappa(2)-C, N)-palladacycles bearing imidazol-2-ylidenes 6 or 7, by either in situ deprotonation or via Ag-NHC intermediate (3), using the bridged palladacycles 4 or 5, respectively. The palladacycles 6 and 7 were characterized by elemental analysis; NMR spectroscopy and the molecular structure of 6c and 7c were determined by X-ray crystallography. The complexes 6 and 7 display high activity in Suzuki-Miyaura coupling of a range of aryl bromides. (C) 2009 Elsevier B.V. All rights reserved.