Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 695, Issue 10-11, Pages 1555-1560Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2010.03.013
Keywords
N-heterocyclic carbene; Palladium catalysis; Amination; Triarylamines; Amines
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Funding
- Technological and Scientific Research Council of Turkey TUB_ITAK-CNRS (France) [TBAG-U/181 (106T716)]
- Inonu University Research Fund [I.U. B.A.P: 2009/10]
- University Research Fund [F279]
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Transmetalation has proved to be a promising procedure to obtain NHC-metal complexes, which typically involves treatment of the imidazolium salt with Ag2O to form the Ag-NHC complex, followed by transmetalation to a species such as [PdCl2(CH3CN)(2)] gave the palladium complex in which the N-heterocyclic carbene was bound to the metal center. New bis(NHC)-Pd complexes were synthesized and characterized by elemental analysis, H-1 NMR, C-13 NMR, and IR spectroscopy. The crystal and molecular structure of the trans-dichlorobis{1-(2,3,5,6-tetramethylbenzyl)-3-(2,3,4,5,6-pentamethylbenzyl)imidazolidin-2-yliden}palladium(II) complex was determined by single-crystal X-ray diffraction. The activity of the Pd(II) complexes in the coupling reaction of anilines or amines with bromobenzene was investigated. A preliminary catalytic study showed that these bis(NHC)-Pd complexes were highly active in the direct synthesis of triarylamines and secondary amines in a single step. (C) 2010 Elsevier B.V. All rights reserved.
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