期刊
ACS CATALYSIS
卷 8, 期 4, 页码 3091-3103出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b04442
关键词
heterogeneous catalysis; methylation; borrowing-hydrogen reaction; platinum; density functional theory
资金
- JSPS KAKENHI from the Japan Society for the Promotion of Science (JSPS) [17H01341, 16H06595]
- Japanese Ministry of Education, Culture, Sports, Science, and Technology (MEXT)
- JST-CREST [JPMJCR17J3]
- Grants-in-Aid for Scientific Research [17H01341] Funding Source: KAKEN
A versatile, selective, and recyclable heterogeneous catalytic method for the methylation of C-H bonds in alcohols, ketones, and indoles with methanol under oxidant-free conditions using a Pt-loaded carbon (Pt/C) catalyst in the presence of NaOH is reported. This catalytic system is effective for various methylation reactions: (1) the beta-methylation of primary alcohols, including aryl, aliphatic, and heterocyclic alcohols, (2) the alpha-methylation of ketones, and (3) the selective C3-methylation of indoles. The reactions are driven by a borrowing-hydrogen mechanism. The reaction begins with the dehydrogenation of the alcohol(s) to afford aldehydes, which subsequently undergo a condensation reaction with the nucleophile (aldehyde, ketone, or indole), followed by hydrogenation of the condensation product by Pt-H species to yield the desired product. In all of the methylation reactions explored in this study, the Pt/C catalyst exhibits a significantly higher turnover number than other previously reported homogeneous catalytic systems. Moreover, it is demonstrated that the high catalytic activity of Pt can be rationalized in terms of the adsorption energy of hydrogen on the metal surface, as revealed by density functional theory calculations on different metal surfaces.
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