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

Authors

  • 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
Further Information

Publication History

Received: 17 February 2015

Accepted after revision: 09 March 2015

Publication Date:
16 April 2015 (online)


Graphical Abstract

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