23062-49-9Relevant articles and documents
Palladium catalyzed oxidation of biorenewable β-citronellol and geraniol for the synthesis of polyfunctionalized fragrances
Venancio, Aldino N.,Menini, Luciano,Maronde, Daiane N.,Gusevskaya, Elena V.,Parreira, Luciana A.
, (2021)
β-Citronellol and geraniol are bio-renewable compounds found in essential oils of various plants. Allylic oxidation of trisubstituted sterically highly encumbered carbon-carbon double bonds in their molecules with dioxygen can be efficiently catalyzed by the palladium acetate/p-benzoquinone combination under 5?10 atm of dioxygen pressure without the need for conventionally used metal co-catalysts. Both substrates gave allyl acetates in ca. 90% combined yield. The oxidation of geraniol proceeded with excellent site-selectivity involving only one of its two C[dbnd]C bonds. Geraniol gave both linear and branched allyl acetates in comparable yields, whereas the reaction of β-citronellol showed high regioselectivity for the corresponding branched product. Polyfunctionalized oxygenated terpenes produced from β-citronellol and geraniol are of a potential importance as ingredients for fragrance compositions.
