Journal
JOURNAL OF THE JAPAN PETROLEUM INSTITUTE
Volume 57, Issue 3, Pages 95-108Publisher
JAPAN PETROLEUM INST
DOI: 10.1627/jpi.57.95
Keywords
Synergistic catalysis; Heterogeneous catalyst; Acid-base catalyst; Nucleophilic addition-reaction; Palladium
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Funding
- Grants-in-Aid for Scientific Research [24686092, 25630362] Funding Source: KAKEN
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This review paper treats with acid-base and Pd-complex-base bifunctional catalyst surfaces used to catalyze nucleophilic addition reactions. A silica-alumina-supported tertiary amine was found to be a highly active heterogeneous catalyst for Michael additions and cyano-ethoxycarbonylation. These reactions barely proceeded with either a homogeneous amine or silica-alumina support, indicating that synergistic catalysis occurred between the silica-alumina surface and basic amine. Silica-alumina, which contains both tertiary and primary amines, was an efficient catalyst for one-pot synthesis of 1,3-dinitroalkanes from aldehydes and nitromethane. The acid-base synergistic catalysis was applied to metal complex-base synergistic catalysis. Both the Pd-complex and tertiary amine-immobilized silica was an excellent heterogeneous catalyst for the Tsuji-Trost reaction. Spectroscopic analyses, such as solid-state MAS NMR, revealed the structures of prepared catalysts, immobilization mechanism of amine groups on the silica-alumina surface, and reaction intermediates and catalytic reaction mechanism. Substrate scope for the cyanation, Michael reaction, 1,3-dinitroalkane synthesis, and the Tsuji-Trost reaction are also described.
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