Synlett 2015; 26(09): 1179-1184
DOI: 10.1055/s-0034-1380196
letter
© Georg Thieme Verlag Stuttgart · New York

A Simple Procedure for the Oxidation of Alcohols Using [Bis(acetoxy)iodo]benzene and a Catalytic Amount of Bromide Ions in Ethyl Acetate

Anna Maria Pia Salvo
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   eMail: michelangelo.gruttadauria@unipa.it
,
Vincenzo Campisciano
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   eMail: michelangelo.gruttadauria@unipa.it
,
Hazi Ahmad Beejapur
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   eMail: michelangelo.gruttadauria@unipa.it
,
Francesco Giacalone
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   eMail: michelangelo.gruttadauria@unipa.it
,
Michelangelo Gruttadauria*
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   eMail: michelangelo.gruttadauria@unipa.it
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Publikationsverlauf

Received: 17. Februar 2015

Accepted after revision: 09. März 2015

Publikationsdatum:
16. April 2015 (online)


Abstract

Primary and secondary benzylic alcohols and secondary aliphatic alcohols were oxidized to the corresponding aldehydes and ketones by using [bis(acetoxy)iodo]benzene (BAIB) and a catalytic amount of bromide ions, from tetrabutylammonium bromide or KBr, in ethyl acetate. The catalytic role of the bromide ions was also highlighted in the oxidation of primary aliphatic alcohols and secondary allylic alcohols carried out in the presence of 1 mol% TEMPO.

Supporting Information

 
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