23399-13-5Relevant academic research and scientific papers
Regioselective Wacker oxidation of internal alkenes: Rapid access to functionalized ketones facilitated by cross-metathesis
Morandi, Bill,Wickens, Zachary K.,Grubbs, Robert H.
, p. 9751 - 9754 (2013)
Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross-metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone. Copyright
PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
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Paragraph 0155, (2014/07/22)
The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.
