Palladium complexes with carbene and phosphine ligands: Synthesis, structural characterization, and direct arylation reactions between aryl halides and alkynes

Kai Ting Chan, Yi Hua Tsai, Wu Shien Lin, Jia Rong Wu, Shih Jung Chen, Fu Xing Liao, Ching-Han Hu, Hon Man Lee

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Abstract

The new palladium complexes with NHC and phosphine ligands, cis-PdCl 2(L2)(PPh3) (2), cisPdBr2(L 2)(PPh3) (3), and cis-PdCl2(L 3)(PPh3) (4) were prepared following a general protocol of a one pot reaction between PdCl2(COD), PPh3, and the ligand precursors LH · Y (Y = Cl, Br, BF4) (L2 = l,3-dibenzylimidazolin-2-ylidene; L3 = l,3-dibenzylimidazol-2- ylidene). The cis-PdCl2(L3)(PCy3) complex (5) was prepared by the ligand substitution reaction between 4 and PCy3. The palladium complexes with NHC and pyridine complexes, trans-PdCl 2(L)(py) (6: L = L2; 7: L = L3) were obtained by heating a mixture Of PdCl2(COD) and LH · BF4 in pyridine. A similar reaction condition using CH3CN as solvent with KO'Bu as base afforded cis-PdCl2(L3)2 (8). Complexes 2-8 were successfully characterized by X-ray crystallographic studies, among which, intriguingly, two polymorphs of 8 were obtained. Thermogravimetric analysis showed that the Cis-PdX2(NHC)(PR3) complexes are more thermally stable than the trans-PdCl2(NHC)(py) complexes. Together with the known Cis-PdCl2(L1(PCy3) (1) (L1 = l-benzyl-3-(N-phenylacetamido)imidazol-2-ylidene), they were screened for the direct arylation reaction between aryl halides and alkynes. The result indicate that the carbene/phosphine complexes 1-5 are superior precatalysts than 6-8 with higher activities than the commonly-used system of Pd(OAc)2/2PPh3.

Original languageEnglish
Pages (from-to)463-472
Number of pages10
JournalOrganometallics
Volume29
Issue number2
DOIs
Publication statusPublished - 2010 Jan 25

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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