Mercaptopropyl-Modified Mesoporous Silica: A Remarkable Support for the Preparation of a Reusable, Heterogeneous Palladium Catalyst for Coupling Reactions
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- 23 June 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (28) , 10045-10050
- https://doi.org/10.1021/ja0430954
Abstract
The functionalization of SBA-15 with mercaptopropyl trimethoxysilane leads to a material capable of absorbing Pd from organic and aqueous solutions. The resulting Pd-loaded material acts as a catalyst for the Suzuki−Miyaura and Mizoroki−Heck coupling reactions. Leaching studies show that the filtrate contains as little as 3 ppb Pd after reaction. Aminopropylated silica is an effective scavenger, and catalyst for the Mizoroki−Heck reaction, but leaching is significant (35 ppm), illustrating the importance of the thiol ligand to retain Pd on the surface. Heterogeneity tests such as hot filtration experiments and three-phase tests show that the reaction is occurring predominantly via surface-bound Pd.Keywords
This publication has 67 references indexed in Scilit:
- The Role of Pd Nanoparticles in Ionic Liquid in the Heck ReactionJournal of the American Chemical Society, 2005
- Mechanistic Studies of SCS-Pd Complexes Used in Heck CatalysisAdvanced Synthesis & Catalysis, 2005
- Evidence that SCS Pincer Pd(II) Complexes are only Precatalysts in Heck Catalysis and the Implications for Catalyst Recovery and ReuseAdvanced Synthesis & Catalysis, 2005
- Thermomorphic fluorous imine and thioether palladacycles as precursors for highly active Heck and Suzuki catalysts; evidence for palladium nanoparticle pathwaysNew Journal of Chemistry, 2002
- Palladium-Catalyzed Coupling Reactions of Aryl ChloridesAngewandte Chemie International Edition in English, 2002
- Synthesis and immobilization of N-heterocyclic carbene complexes of Ru(II): catalytic activity and recyclability for the furan formationJournal of Molecular Catalysis A: Chemical, 2002
- Control of Pd leaching in Heck reactions of bromoarenes catalyzed by Pd supported on activated carbonJournal of Molecular Catalysis A: Chemical, 2001
- Cyclopalladated imine catalysts in Heck arylation: search for the catalytic speciesChemical Communications, 2000
- Three-phase test for reaction intermediates. Nucleophilic catalysis and elimination reactionsJournal of the American Chemical Society, 1975
- Three-phase test for reactive intermediates. CyclobutadieneJournal of the American Chemical Society, 1974