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

A series of imidzoalium salt, L · HCl, for the potentially bidentate pyrazole/ N-heterocyclic carbene was synthesized. Structural determinations reveal that compounds based on pyrazole/imidazolium chloride L · HCl adopt gauche conformation exclusively in the solid state. Palladium complexes of L · H...

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Published inJournal of organometallic chemistry Vol. 690; no. 2; pp. 403 - 414
Main Authors Lee, Hon Man, Chiu, Pei Ling, Hu, Ching-Han, Lai, Chun-Liang, Chou, Yi-Chun
Format Journal Article
LanguageEnglish
Published LAUSANNE Elsevier B.V 01.01.2005
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Gauche preference
Heck reaction
Imidazolium chlorides
Palladium complex
Physical Sciences
Pyrazole
Science & Technology
X-ray determination
X-ray determination
Heck reaction
Palladium complex
Gauche preference
Imidazolium chlorides
Pyrazole
PALLADIUM COMPLEXES
GAUCHE
SILVER
pyrazole
palladium complex
DENSITY
LIGANDS
imidazolium chlorides
HETEROCYCLIC CARBENE COMPLEXES
C COUPLING REACTIONS
CATALYSTS
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Summary:A series of imidzoalium salt, L · HCl, for the potentially bidentate pyrazole/ N-heterocyclic carbene was synthesized. Structural determinations reveal that compounds based on pyrazole/imidazolium chloride L · HCl adopt gauche conformation exclusively in the solid state. Palladium complexes of L · HCl are active Heck catalysts. 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.
ISSN:0022-328X
1872-8561
DOI:10.1016/j.jorganchem.2004.09.053