Structures and Suzuki-Coupling of N-Heterocyclic Carbene Complexes of PdII with Coordinated Solvent and PPh3

Swee Kuan Yen; Lip Lin Koh; Han Vinh Huynh; T. S. Andy Hor

doi:10.1071/CH09196

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Structures and Suzuki-Coupling of N-Heterocyclic Carbene Complexes of Pd^II with Coordinated Solvent and PPh₃

Swee Kuan Yen ^A , Lip Lin Koh ^A , Han Vinh Huynh ^A and T. S. Andy Hor ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, National University of Singapore, Kent Ridge, 117543, Singapore.

^B Corresponding author. Email: andyhor@nus.edu.sg

Australian Journal of Chemistry 62(9) 1047-1053 https://doi.org/10.1071/CH09196
Submitted: 7 April 2009 Accepted: 25 May 2009 Published: 17 September 2009

Abstract

A series of mononuclear N,N-heterocyclic carbene (NNHC) complexes of Pd^II with mixed ligands of 1,3-dibenzylbenzimidazoly-2-ylidene and solvate (dimethyl sulfoxide, CH₃CN, N,N-dimethylformamide, and pyridine) or PPh₃ were prepared and characterized by X-ray single-crystal diffraction analysis. They are more active in the Suzuki–Miyaura coupling of selected aryl bromides than their N,S-heterocyclic carbene (NSHC) analogues.

^* PEPPSI = Pyridine-enhanced Precatalyst, Preparation, Stabilization, and Initiation catalyst with N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) ligand. This commercially available catalyst has been developed as an air-stable catalyst to promote cross-coupling reactions. See Ref. [2].

Acknowledgement

The authors thank the National University of Singapore (NUS), Ministry of Education (R-143-000-361-112) and Agency for Science, Technology and Research (R-143-000-364-305) for financial support as well as the staff at the CMMAC of NUS for technical assistance. S.K.Y. acknowledges NUS for the research scholarship and K. E. Neo for discussion.

References

Structures and Suzuki-Coupling of N-Heterocyclic Carbene Complexes of PdII with Coordinated Solvent and PPh3

Abstract

Acknowledgement

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Structures and Suzuki-Coupling of N-Heterocyclic Carbene Complexes of Pd^II with Coordinated Solvent and PPh₃