期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 17, 页码 6111-6119出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201505109
关键词
alcohols; heterogeneous catalysis; olefination; platinum; sulfones
资金
- JSPS KAKENHI [26289299]
- MEXT program Elements Strategy Initiative to Form Core Research Center
- JSPS [25106010]
- Grants-in-Aid for Scientific Research [25106010, 26289299] Funding Source: KAKEN
Carbon-supported Pt nanoparticles (Pt/C) were found to be effective heterogeneous catalysts for the direct Julia olefination of alcohols in the presence of sulfones and KOtBu under oxidant-free conditions. Primary alcohols, including aryl, aliphatic, allyl, and heterocyclic alcohols, underwent olefination with dimethyl sulfone and aryl alkyl sulfones to give terminal and internal olefins, respectively. Secondary alcohols underwent methylenation with dimethyl sulfone. Under 2.5bar H-2,H- the same reaction system was effective for the transformation of alcohol OH groups to alkyl groups. Structural and mechanistic studies of the terminal olefination system suggested that Pt-0 sites on the Pt metal particles are responsible for the rate-limiting dehydrogenation of alcohols and that KOtBu may deprotonate the sulfone reagent. The Pt/C catalyst was reusable after the olefination, and this method showed a higher turnover number (TON) and a wider substrate scope than previously reported methods, which demonstrates the high catalytic efficiency of the present method.
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