Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl

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Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl

The 1,3-diaryl-imidazolium chlorides IPr.HCl (aryl = 2,6-diisopropylphenyl), IMes.HCl (aryl = 2,4,6-trimethylphenyl) and IXy.HCl (aryl = 2,6-dimethylphenyl), precursors to widely used N-heterocyclic carbene (NHC) ligands and catalysts, were prepared in high yields (81%, 69% and 89%, respectively) by the reaction of 1,4-diaryl-1, 4-diazabutadienes, paraformaldehyde and chlorotrimethylsilane in d...

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Structure and reactivity of "unusual" N-heterocyclic carbene (NHC) palladium complexes synthesized from imidazolium salts.

The reaction between palladium acetate and IMES.HCl leads to the formation of a novel palladium complex. The X-ray crystal structure analysis reveals that the palladium is C(2) bound to one NHC ligand (the normal binding mode), whereas the second ligand is attached through the C(5) carbon of the second imidazolium. The metalation site on the imidazolium salt is strongly influenced by the presen...

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Shape-Controllable Formation of Poly-imidazolium Salts for Stable Palladium N-Heterocyclic Carbene Polymers

The imidazolium-based main-chain organic polymers are one of promising platforms in heterogeneous catalysis, the size and outer morphology of polymer particles are known to have important effects on their physical properties and catalytic applications, but main-chain ionic polymers usually generate amorphous or spherical particles. Herein, we presented a versatile and facile synthetic route for...

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Carbene-anchored/pendent-imidazolium species as precursors to di-N-heterocyclic carbene-bridged mixed-metal complexes.

Reaction of a series of linked diimidazolium dibromide salts with one-half equivalent of [Rh(mu-OAc)(COD)](2) under reflux conditions generates a series of carbene-anchored/pendent-imidazolium complexes, [RhBr(COD)((R)C(H)-eta(1)-C(eth))][Br] ((Me)C(H)-eta(1)-C(eth) = ethylene[(N-methyl)imidazolium][(N-methyl)imidazole-2-ylidene] and (tBu)C(H)-eta(1)-C(eth) = ethylene[(N-tert-butyl)imidazolium]...

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Sulfur-functionalized N-heterocyclic carbene complexes of Pd(II): syntheses, structures and catalytic activities.

N-heterocyclic carbenes (NHCs) can be easily modified by introducing functional groups at the nitrogen atoms, which leads to versatile coordination chemistry as well as diverse catalytic applications of the resulting complexes. This article summarizes our contributions to the field of NHCs bearing different types of sulfur functions, i.e., thioether, sulfoxide, thiophene, and thiolato. The expe...

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ژورنال

عنوان ژورنال: Beilstein Journal of Organic Chemistry

سال: 2007

ISSN: 1860-5397

DOI: 10.1186/1860-5397-3-22