Synlett 2014; 25(20): 2923-2927
DOI: 10.1055/s-0034-1378913
letter
© Georg Thieme Verlag Stuttgart · New York

TEMPO/NBu4Br-Catalyzed Selective Alcohol Oxidation with Periodic Acid

Mariam Attoui
Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS, Equipe SURCOOF, bât. Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France   Fax: +33(4)72431214   eMail: vatele@univ-lyon1.fr
,
Jean-Michel Vatèle*
Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS, Equipe SURCOOF, bât. Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France   Fax: +33(4)72431214   eMail: vatele@univ-lyon1.fr
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Publikationsverlauf

Received: 15. September 2014

Accepted: 02. Oktober 2014

Publikationsdatum:
29. Oktober 2014 (online)


Abstract

Oxidation of primary and secondary alcohols, using catalytic amounts of TEMPO and tetra-n-butylammonium bromide in combination with periodic acid and wet alumina in dichloromethane is described. This oxidizing system is compatible with a broad range of functional groups and acid-sensitive protecting groups. Chemoselective oxidation of secondary alcohols in the presence of primary alcohols was observed.