Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 6, Issue 11, Pages 1628-1634Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201700337
Keywords
industrial chemistry; oxidation; oxygen; palladium; renewable resources
Categories
Funding
- CNPq (Brazil)
- FAPEMIG (Brazil)
- CAPES (Brazil)
- INCT Catalise (Brazil)
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alpha-Ionone and beta-ionone are natural products that are found in a variety of essential oils and are also produced synthetically on an industrial scale. Both ionones were selectively oxidized by molecular oxygen in the presence of chloride-free Pd(OAc)(2)/para-benzoquinone catalytic systems. Highly functionalized oxygenated terpenoids that were obtained in these new processes are potentially useful as ingredients in synthetic perfumes, cosmetics, and pharmaceuticals. beta-Ionone (known as rose ketone) was converted into a single major product, whereas alpha-ionone gave three isomeric products, all of which resulted from the allylic oxidation of their endocyclic double bonds. These processes operated with an efficient dioxygen-coupled catalytic turnover under 5-10 atm pressure, in the absence of conventionally used metal-redox-active cocatalysts. Alternatively, the reactions could be efficiently conducted under atmospheric pressure in the presence of copper acetate to assist in the regeneration of BQ by molecular oxygen.
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