The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Aug. 04, 2015

Filed:

Jan. 08, 2014
Applicant:

California Institute of Technology, Pasadena, CA (US);

Inventors:

Bill Morandi, Pasadena, CA (US);

Robert H. Grubbs, South Pasadena, CA (US);

Zachary K. Wickens, Pasadena, CA (US);

Michael M. Lerch, Pasadena, CA (US);

Assignee:
Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07C 303/30 (2006.01); C07C 303/40 (2006.01); C07D 209/48 (2006.01); C07C 45/28 (2006.01); C07C 67/29 (2006.01); C07C 201/12 (2006.01); C07C 231/12 (2006.01); C07C 247/04 (2006.01); C07C 67/313 (2006.01); C07C 51/373 (2006.01); C07B 41/06 (2006.01);
U.S. Cl.
CPC ...
C07D 209/48 (2013.01); C07B 41/06 (2013.01); C07C 45/28 (2013.01); C07C 51/373 (2013.01); C07C 67/29 (2013.01); C07C 67/313 (2013.01); C07C 201/12 (2013.01); C07C 231/12 (2013.01); C07C 247/04 (2013.01); C07C 303/30 (2013.01); C07C 303/40 (2013.01); C07C 2101/14 (2013.01);
Abstract

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 Ccarbon 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.


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