Synthesis and structural characterization of metal complexes based on pyrazole/imidazolium chlorides

Hon Man Lee, Pei Ling Chiu, Ching Han Hu, Chun Liang Lai, Yi Chun Chou

Research output: Contribution to journalArticle

72 Citations (Scopus)

Abstract

A series of imidzoalium salt, L • HCl, for the potentially bidentate pyrazole/N-heterocyclic carbene was synthesized. Reactions of a 2:1 mixture between L • HCl bearing bulky N-substitution and Ag 2O produced Ag(L)Cl, whereas a novel compound with unique stoichiometry AgL 2(AgCl) 0.5Cl was produced from L • HCl bearing N-methyl group under identical condition. Reactions of L • HCl with PdCl 2 produced zwitterionic Pd IICl 3L • H. Selected structural determinations on L • HCl, Ag(L)Cl, AgL 2(AgCl) 0.5Cl, and Pd IICl 3L • H revealed intriguing crystal chemistry in which the less-stable gauche rotamers were obtained exclusively. A preliminary application of the zwitterionic complexes, Pd IICl 3L • H, in Heck coupling reaction of aryl bromide with n-butyl acrylate shows effective activity.

Original languageEnglish (US)
Pages (from-to)403-414
Number of pages12
JournalJournal of Organometallic Chemistry
Volume690
Issue number2
DOIs
StatePublished - Jan 17 2005
Externally publishedYes

Fingerprint

Bearings (structural)
Coordination Complexes
Metal complexes
Bromides
Salts
chlorides
Crystal chemistry
synthesis
Stoichiometry
metals
Substitution reactions
carbenes
acrylates
bromides
stoichiometry
substitutes
chemistry
salts
crystals
imidazole

Keywords

  • Gauche preference
  • Heck reaction
  • Imidazolium chlorides
  • Palladium complex
  • Pyrazole
  • X-ray determination

ASJC Scopus subject areas

  • Chemical Engineering (miscellaneous)
  • Materials Science (miscellaneous)
  • Materials Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Biochemistry

Cite this

Synthesis and structural characterization of metal complexes based on pyrazole/imidazolium chlorides. / Lee, Hon Man; Chiu, Pei Ling; Hu, Ching Han; Lai, Chun Liang; Chou, Yi Chun.

In: Journal of Organometallic Chemistry, Vol. 690, No. 2, 17.01.2005, p. 403-414.

Research output: Contribution to journalArticle

Lee, Hon Man ; Chiu, Pei Ling ; Hu, Ching Han ; Lai, Chun Liang ; Chou, Yi Chun. / Synthesis and structural characterization of metal complexes based on pyrazole/imidazolium chlorides. In: Journal of Organometallic Chemistry. 2005 ; Vol. 690, No. 2. pp. 403-414.
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AU - Chou, Yi Chun

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AB - A series of imidzoalium salt, L • HCl, for the potentially bidentate pyrazole/N-heterocyclic carbene was synthesized. Reactions of a 2:1 mixture between L • HCl bearing bulky N-substitution and Ag 2O produced Ag(L)Cl, whereas a novel compound with unique stoichiometry AgL 2(AgCl) 0.5Cl was produced from L • HCl bearing N-methyl group under identical condition. Reactions of L • HCl with PdCl 2 produced zwitterionic Pd IICl 3L • H. Selected structural determinations on L • HCl, Ag(L)Cl, AgL 2(AgCl) 0.5Cl, and Pd IICl 3L • H revealed intriguing crystal chemistry in which the less-stable gauche rotamers were obtained exclusively. A preliminary application of the zwitterionic complexes, Pd IICl 3L • H, in Heck coupling reaction of aryl bromide with n-butyl acrylate shows effective activity.

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KW - Heck reaction

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