Allylic Oxidation of Alkenes Catalyzed by a Copper–Aluminum Mixed Oxide | Zendy

Ana Leticia GarcíaCabeza | Zendy; Rubén MarínBarrios | Zendy; F. Javier MorenoDorado | Zendy; Marı́a J. Ortega | Zendy; Guillermo M. Massanet | Zendy; Francisco M. Guerra | Zendy

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Allylic Oxidation of Alkenes Catalyzed by a Copper–Aluminum Mixed Oxide

Author(s) -

Ana Leticia GarcíaCabeza,

Rubén MarínBarrios,

F. Javier MorenoDorado,

Marı́a J. Ortega,

Guillermo M. Massanet,

Francisco M. Guerra

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol500198c

Subject(s) - allylic rearrangement , chemistry , alkene , catalysis , cyclohexene , ketone , copper , oxide , alcohol , allylic alcohol , organic chemistry

A strategy for the allylic oxidation of cyclic alkenes with a copper-aluminum mixed oxide as catalyst is presented. The reaction involves the treatment of an alkene with a carboxylic acid employing tert-butyl hydroperoxide as the oxidant. In all cases, the corresponding allylic esters are obtained. When L-proline is employed, the allylic alcohol or ketone is obtained. The oxidation of cyclohexene and valencene has been optimized by design of experiments (DoE) statistical methodology.

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