Oxidation of terminal olefins with Tetrakis(Triphenylphosphine)Palladium(0)Gazz Chim Ital 122, 531-532 (1992) (English)
Solvent: 3.2M aqueous H2O2 solution.
Reaction conditions: 72h stirring at ~50°C.
Catalysis statistics: 2000:1 molar ratio alkene:catalyst
Conversion & Selectivity: 99%+
Summary-
Terminal Olefins can be oxidised under mild conditions in exellent yields and selectivities to methyl ketones by employing an auqeous medium containing hydrogen peroxide as the oxidant and tetrakis(triphenylphosphine)palladium(0) as the catalyst.
Palladium(0)-catalysed oxidation of terminal alkenes with Hydrogen Peroxide in a heterogeneous aqueous medium.
Olefin / Product / Conversion / Selectivity / Reaction Temp.
-
1-hexene / 2-hexanone / >99% / >99% / 40°C
1-heptene / 2-heptanone / >99% / >99% / 50°C
1-octene / 2-octanone / 98% / >99% / 50°C
1-decene / 2-decanone / 98% / >99% / 80°C
1-octadecene / 2-octadecanone / 10% >99% / 80°C
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Rhodium posted this in the Serious Chemistry Forum a while back. Has anyone else taken a look at this? If this will work with Safrole, and I see no reason why it wouldn't, we would have the perfect method. Minimal equipment, easy procedure, no isomerized alkene, it seems perfect to me.
In case you were wondering, Tetrakis(Triphenylphosphine)Palladium(0) is used in industry, and is available from all the major chem companies (Alfa, TCI, Etc.) for a fair price, about the same or cheaper than PdCl2. Plus, you are using only a fraction of the amount (5g for 100g olefin as opossed to 500mg for 100g olefin). And it is totally unwatched.
Any thoughts/comments? I am going to try and give it a runs as soon as I can get my hands on the catalyst.
