Palladium containing nanostructured silica functionalized with pyridine sites: a versatile heterogeneous catalyst for Heck, Sonogashira, and cyanation reactions

Nanostructured hybrid silica bearing pyridine binding sites was prepared in a template assisted hydrolysis–polycondensation of tetraethylorthosilicate (TEOS) and the ionic precursor N, N-dimethyl-pyridin-4-yl-(3-triethoxysilyl-propyl)-ammonium iodide using N-dodecyl- N′-methyl-imidazolium bromide as...

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Bibliographic Details
Published in:Tetrahedron 2007-07, Vol.63 (29), p.6784-6790
Main Authors: Polshettiwar, Vivek, Hesemann, Peter, Moreau, Joël J.E.
Format: Article
Language:English
Subjects:
Chemical Sciences
Cyanation
Heck reaction
Imidazolium salts
Material chemistry
Nanostructured hybrid silica
Organic chemistry
Sonogashira reaction
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Summary:Nanostructured hybrid silica bearing pyridine binding sites was prepared in a template assisted hydrolysis–polycondensation of tetraethylorthosilicate (TEOS) and the ionic precursor N, N-dimethyl-pyridin-4-yl-(3-triethoxysilyl-propyl)-ammonium iodide using N-dodecyl- N′-methyl-imidazolium bromide as structure directing agent. After treatment with palladium acetate, the material appeared as a versatile heterogeneous catalyst for Heck, Sonogashira, and cyanation reactions. In Heck and Sonogashira cross-coupling reactions, unchanged catalytic activity was observed in at least five reaction cycles. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.04.073