Palladium-Catalyzed Aerobic Oxidation of Naturally Occurring Allylbenzenes as a Route to Valuable Fragrance and Pharmaceutical Compounds

• Published in: Advanced synthesis & catalysis Vol. 352; no. 9; pp. 1533 - 1538
• Main Authors: Parreira, Luciana A., Menini, Luciano, da Cruz Santos, Joyce C., Gusevskaya, Elena V.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-06-2010; WILEY‐VCH Verlag
• Subjects: allylbenzenes; Catalysis; Catalysts; Chlorides; Economics; Flavours; Ligands; methyl ketones; Oxidation; oxygen; palladium; Pharmaceuticals
• ISSN: 1615-4150; 1615-4169; 1615-4169
• DOI: 10.1002/adsc.201000050

A palladium‐catalyzed, aerobic oxidation of naturally occurring allylbenzenes, i.e., eugenol, methyleugenol, safrole, and estragole, in dimethylacetamide/water solutions under mild conditions has been developed, in which palladium(II) chloride is used in the absence of co‐catalysts or special stabilizing ligands as the sole and recyclable catalyst. Methyl ketones that are important for the flavour and pharmaceutical industries have been obtained in good to excellent yields with low catalyst loadings (1–2 mol%) and high average turnover frequencies. This simple catalytic method represents an ecologically benign and economically attractive route to industrially valuable compounds starting from renewable substrates easily available from essential oils.