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

doi:10.1016/j.jorganchem.2004.09.053

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 journal › Article › peer-review

78 Scopus citations

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 language	English (US)
Pages (from-to)	403-414
Number of pages	12
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	2
DOIs	https://doi.org/10.1016/j.jorganchem.2004.09.053
State	Published - Jan 17 2005
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2004.09.053

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title = "Synthesis and structural characterization of metal complexes based on pyrazole/imidazolium chlorides",

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.",

keywords = "Gauche preference, Heck reaction, Imidazolium chlorides, Palladium complex, Pyrazole, X-ray determination",

author = "Lee, {Hon Man} and Chiu, {Pei Ling} and Hu, {Ching Han} and Lai, {Chun Liang} and Chou, {Yi Chun}",

note = "Funding Information: We are grateful to the National Science Council of Taiwan for financial support of this work (Grant NSC 93-2113-M-018-004). ",

year = "2005",

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doi = "10.1016/j.jorganchem.2004.09.053",

language = "English (US)",

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AU - Lee, Hon Man

AU - Chiu, Pei Ling

AU - Hu, Ching Han

AU - Lai, Chun Liang

AU - Chou, Yi Chun

N1 - Funding Information: We are grateful to the National Science Council of Taiwan for financial support of this work (Grant NSC 93-2113-M-018-004).

PY - 2005/1/17

Y1 - 2005/1/17

N2 - 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.

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.

KW - Gauche preference

KW - Heck reaction

KW - Imidazolium chlorides

KW - Palladium complex

KW - Pyrazole

KW - X-ray determination

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

Abstract

Keywords

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