A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction

Hon Man Lee, Pei Ling Chiu, Jing Yao Zeng

Research output: Contribution to journalArticle

92 Citations (Scopus)

Abstract

Ligand precursors, L • HCl (L = (1-R)-(3-diphenylphosphanylethyl)- imidazol-2-ylidene; R = mesity, aryl, naphthylmethyl), for the phosphine-functionalized N-heterocyclic carbene (NHC) were synthesized by a convenient procedure. PdLCl2 (4) were prepared by a one pot reaction of PdCl2, sodium acetate, and L • HCl in DMSO. Catalytic studies have shown that complex 4 is efficient in Suzuki coupling reactions of aryl bromides with phenylboronic acid. A series of imidazolium chlorides as ligand precursors, L • HCl (L = (1-R)-(3-diphenylphosphanylethyl)-imidazol-2- ylidene; R = aryl, benzyl, naphthylmethyl), for the phosphine-functionalized N-heterocyclic carbene (NHC), L, were prepared by a convenient synthetic procedure of reacting 1,2-dichloroethane with appropriate N-substituted imidazoles to give (β-chloroethyl)imidazolium chlorides, which were subsequently reacted with HPPh2 producing L • HCl in good yield. Palladium complexes of L, PdLCl2 (4), were prepared by a one pot reaction of PdCl2, sodium acetate, and L • HCl in DMSO. Complexes 4b (R = naphthylmethyl) and 4e (R = m-methoxybenzyl) were characterized by X-ray crystallography. Catalytic studies have shown that the palladium complexes are efficient in Suzuki coupling reactions of aryl bromides with phenylboronic acid.

Original languageEnglish
Pages (from-to)4313-4321
Number of pages9
JournalInorganica Chimica Acta
Volume357
Issue number14
DOIs
Publication statusPublished - 2004 Nov 15

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Fingerprint Dive into the research topics of 'A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction'. Together they form a unique fingerprint.

  • Cite this