Issue 39, 2013
From the journal:

Chemical Communications

Organocatalytic oxidation of aldehydes to mixed anhydrides†‡

Hila Toledo,a   Evgeni Pisarevsky,a   Adi Abramovicha  and  Alex M. Szpilman*a  

* Corresponding authors

a Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, 32000 Haifa, Israel
E-mail: szpilman@tx.technion.ac.il
Fax: +972-4-8295703
Tel: +972-4-8295953

Abstract

TEMPO catalyzes the direct oxidation of aldehydes to mixed anhydrides in the presence of a carboxylic acid. The anhydrides can be converted in situ to esters, secondary, tertiary or Weinreb amides in high yield. Oxidation of the aldehyde directly to 2-propyl esters is also possible using only catalytic amounts of acid. The oxidation reactions are rapid and take place under mild conditions.

Graphical abstract: Organocatalytic oxidation of aldehydes to mixed anhydrides

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Article information

DOI
https://doi.org/10.1039/C2CC35220F
Article type
Communication
Submitted
19 Jul 2012
Accepted
29 Aug 2012
First published
31 Aug 2012

Chem. Commun., 2013,49, 4367-4369

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Organocatalytic oxidation of aldehydes to mixed anhydrides

H. Toledo, E. Pisarevsky, A. Abramovich and A. M. Szpilman, Chem. Commun., 2013, 49, 4367 DOI: 10.1039/C2CC35220F

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