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Open AccessFeature PaperArticle

Mg-Catalyzed OPPenauer Oxidation—Application to the Flow Synthesis of a Natural Pheromone

Institut des Sciences Moléculaires (ISM), UMR 5255 CNRS—Université de Bordeaux, 351 Cours de la Libération, 33405 Talence CEDEX, France
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Catalysts 2018, 8(11), 529; https://doi.org/10.3390/catal8110529
Received: 3 October 2018 / Revised: 29 October 2018 / Accepted: 2 November 2018 / Published: 8 November 2018
(This article belongs to the Special Issue Catalytic Methods in Flow Chemistry)
The so-called OPPenauer oxidation is well known for its ability to oxidize valuable alcohols into their corresponding aldehydes or ketones. In particular, it has proven to be extremely successful in the oxidation of sterols. On the other hand, its application—in the original formulation—to the obtainment of ketones outside the field of steroids met a more limited success because of less favorable thermodynamics and side reactions. To circumvent these issues, the first example of magnesium-catalyzed OPPenauer oxidation is described. The oxidation of primary and secondary alcohol was performed using pivaldehyde or bromaldehyde as the oxidant and cheap magnesium tert-butoxide as catalyst. Decent to excellent yields were obtained using reasonable catalytic charge. The synthesis of a pheromone stemming from the Rhynchophorus ferrugineus was obtained by tandem addition-oxidation of 2-methylpentanal and the process was successfully applied to continuous flow on a multigram scale. View Full-Text
Keywords: Oppenauer oxidation; magnesium; catalysis; alcohols; aldehydes; ketones; pheromone; Rhynchophorus ferrugineus Oppenauer oxidation; magnesium; catalysis; alcohols; aldehydes; ketones; pheromone; Rhynchophorus ferrugineus
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MDPI and ACS Style

Liautard, V.; Birepinte, M.; Bettoli, C.; Pucheault, M. Mg-Catalyzed OPPenauer Oxidation—Application to the Flow Synthesis of a Natural Pheromone. Catalysts 2018, 8, 529.

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