Palladium Nanoparticle Loaded Bifunctional Silica Hybrid Material: Preparation and Applications as Catalyst in Hydrogenation Reactions

Bifunctional mesoporous silica was prepared by co‐condensation of tetraethyl orthosilicate (TEOS) with functionalized organosilanes containing azides or alkoxyamines. Orthogonal functional groups at the particles were selectively addressed in subsequent chemical modifications through “click”‐chemist...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-05, Vol.23 (25), p.6019-6028
Main Authors: Surmiak, Sabrina K., Doerenkamp, Carsten, Selter, Philipp, Peterlechner, Martin, Schäfer, Andreas H., Eckert, Hellmut, Studer, Armido
Format: Article
Language:English
Subjects:
Catalysts
Chemical reactions
Chemistry
Cleavage
click chemistry
cooperative catalysis
Functional groups
Hydrogenation
Ligands
mesoporous silica
Nanoparticles
NMR spectroscopy
palladium nanoparticles
Silica
Silicon dioxide
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Summary:Bifunctional mesoporous silica was prepared by co‐condensation of tetraethyl orthosilicate (TEOS) with functionalized organosilanes containing azides or alkoxyamines. Orthogonal functional groups at the particles were selectively addressed in subsequent chemical modifications through “click”‐chemistry (“click to ligand” strategy) and radical nitroxide exchange. Palladation with PdCl2 delivered Pd nanoparticle‐loaded silica material bearing sulfoxides and additional aminoamides as stabilizing ligands by means of in situ reduction of the PdII‐salt. These functional particles were successfully applied to the hydrogenation of alkynes and alkenes. Aldehyde hydrodeoxygenation and benzyl ether cleavage were achieved with these hybrid catalysts under mild conditions. Particles were analyzed by IR, TEM/STEM, EDX, and solid‐state NMR spectroscopy. Click‐chemistry: Various palladium nanoparticle‐loaded recyclable bifunctional sulfoxide–aminoamide silica particles were prepared and applied to the semihydrogenation of internal as well as external alkynes. Alkene hydrogenation and deoxygenation of activated alcohols can also be achieved by using these novel functionalized mesoporous catalysts.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201604508