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DOI: 10.1055/s-0033-1340726
A Silicon Nanowire Array Stabilized Palladium-Nanoparticle Catalyst
A Palladium-Nanoparticle and Silicon-Nanowire-Array Hybrid: A Platform for Catalytic Heterogeneous Reactions.
Angew. Chem. Int. Ed. 2014;
53: 127-131
Publication History
Publication Date:
17 February 2014 (online)
Key words
silicon-nanowire array - palladium nanoparticles - Mizoroki–Heck reaction - C–H functionalization
Significance
A silicon nanowire array stabilized palladium-nanoparticle catalyst (SiNA-Pd) for C–H functionalization was developed. Thus, the Mizoroki–Heck reaction of iodobenzene (1, 50 mmol, 10.2 g) and butyl acrylate (2, 2 equiv) proceeded in the presence of SiNA-Pd, Et3N, and tetrabutylammonium acetate (TBAA) to give butyl cinnamate (3) in 95% yield (9.7 g). SiNA-Pd was applied to the C–H functionalization reactions of thiophene 4 and indole 6, the hydrogenation of an alkene, and the hydrosilylation of an enone.
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Comment
The turnover number (TON) of SiNA-Pd was 2 × 106 for the reaction of 1 and 2, which is the highest TON for any Mizoroki–Heck reaction with a heterogeneous catalyst. A thromboxane A2 synthesis inhibitor, (2E)-3-[4-(1H-imidazol-1-ylmethyl)phenyl]acrylic acid (ozagrel), was prepared via the SiNA-Pd-mediated Mizoroki–Heck reaction.
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