Abstract
The palladium catalyzed oxidation is a versatile method for upgrading of cis-jasmone, a main aroma constituent of jasmine essential oil. Although both olefinic bonds in cis-jasmone are sterically hindered, the substrate has demonstrated a remarkable reactivity in Wacker type oxidations. Depending on the catalyst and the solvent, reactions can be directed to either allylic oxidation or ketone products. The oxidation in acetic acid solutions with a chloride-free Pd(OAc)2/p-benzoquinone catalyst gave with high selectivity an allylic acetate. An efficient oxygen-couple catalytic turnover can be achieved either under atmospheric pressure with catalytic amounts of Cu(OAc)2 to promote the regeneration of p-benzoquinone or at 5–10 at m of oxygen in the absence of any auxiliary co-catalyst. Alternatively, cis-jasmone can be oxidized to ketone products in aqueous dimethylacetamide solutions using molecular oxygen as a final oxidant and PdCl2 as a sole catalyst. Poly-functionalized jasmonoids obtained are potentially useful as components of perfumes and cosmetics.
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