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

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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. PdLCl 2 (4) were prepared by a one pot reaction of PdCl 2, 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 HPPh 2 producing L • HCl in good yield. Palladium complexes of L, PdLCl 2 (4), were prepared by a one pot reaction of PdCl 2, 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

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phosphine
Sodium Acetate
Palladium
carbenes
Dimethyl Sulfoxide
Bromides
phosphines
palladium
imidazoles
Ligands
Sodium
Imidazoles
ligands
Acids
X ray crystallography
synthesis
bromides
acetates
chlorides
sodium

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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title = "A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction",
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. PdLCl 2 (4) were prepared by a one pot reaction of PdCl 2, 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 HPPh 2 producing L • HCl in good yield. Palladium complexes of L, PdLCl 2 (4), were prepared by a one pot reaction of PdCl 2, 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.",
author = "Lee, {Hon Man} and Chiu, {Pei Ling} and Zeng, {Jing Yao}",
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T1 - A convenient synthesis of phosphine-functionalized N-heterocyclic carbene ligand precursors, structural characterization of their palladium complexes and catalytic application in Suzuki coupling reaction

AU - Lee, Hon Man

AU - Chiu, Pei Ling

AU - Zeng, Jing Yao

PY - 2004/11/15

Y1 - 2004/11/15

N2 - 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. PdLCl 2 (4) were prepared by a one pot reaction of PdCl 2, 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 HPPh 2 producing L • HCl in good yield. Palladium complexes of L, PdLCl 2 (4), were prepared by a one pot reaction of PdCl 2, 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.

AB - 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. PdLCl 2 (4) were prepared by a one pot reaction of PdCl 2, 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 HPPh 2 producing L • HCl in good yield. Palladium complexes of L, PdLCl 2 (4), were prepared by a one pot reaction of PdCl 2, 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.

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