eCite Digital Repository

Donor-Functionalized Heterocyclic Carbene Complexes of Palladium (II): Efficient Catalysts for C-C Coupling Reactions

Citation

McGuinness, DS and Cavell, KJ, Donor-Functionalized Heterocyclic Carbene Complexes of Palladium (II): Efficient Catalysts for C-C Coupling Reactions, Organometallics, 19, (5) pp. 741-748. ISSN 0276-7333 (2000) [Refereed Article]

DOI: doi:10.1021/om990776c

Abstract

Pd II complexes of donor-functionalized heterocyclic carbene ligands have been synthesized through a route involving carbene transfer from Ag I carbene precursors. The Ag complexes undergo facile reaction with PdCl 2(MeCN) 2 to yield Pd(C∧OPh) 2Cl 2 (3a), Pd(C∧OOMe) 2Cl 2 (3b), and Pd(C∧N) 2Cl 2 (3c) (C∧OPh = 3-methyl-1-phenacylimidazolin-2-ylidene, C∧OOMe = 3-methyl-1-(methylacetyl)imidazolin-2-ylidene, C∧N = 3-methyl-1-picolylimidazolin-2-ylidene), from which [Pd(C∧OOMe) 2(MeCN) 2][BF 4] 2 (4b) and [Pd(C∧N) 2][BF 4] 2 (4c) can be prepared by halide abstraction. When PdMeCl(cod) (cod = cyclooctadiene) is treated with the Ag complexes 2b and 2c, the Me-Pd carbene complexes [PdMe(C∧OOMe)Cl] 2 (5b), PdMe-(C∧N)Cl (5c), PdMe(C∧OOMe) 2Cl (6b), and PdMe(C∧N) 2Cl (6c) are obtained. The C∧OPh and CAOOMe ligands are monodentate with a dangling functional moiety in all complexes, while the CAN ligand exhibits both monodentate and chelating behavior. Several complexes give rise to highly active and very stable catalysts for Heck, Suzuki, and Sonogashira coupling reactions, with turnover numbers of up to 1 700 000 (Heck) and 127 500 (Suzuki) being obtained.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Other Chemical Sciences
Research Field:Organometallic Chemistry
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
Author:McGuinness, DS (Dr David McGuinness)
Author:Cavell, KJ (Professor Kingsley Cavell)
ID Code:19735
Year Published:2000
Web of Science® Times Cited:492
Deposited By:Chemistry
Deposited On:2000-08-01
Last Modified:2011-08-04
Downloads:0

Repository Staff Only: item control page