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: [email protected]
,
Vincenzo Campisciano
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   Email: [email protected]
,
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: [email protected]
,
Francesco Giacalone
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   Email: [email protected]
,
Michelangelo Gruttadauria*
Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università di Palermo, Viale delle Scienze, Ed. 17, 90128 Palermo, Italy   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 17 February 2015

Accepted after revision: 09 March 2015

Publication Date:
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

 
  • References

  • 1 Patel S, Mishra BK. Tetrahedron 2007; 63: 4367
  • 2 Ooms PH. J, Scheeren JW, Nivard RJ. F. Synthesis 1975; 639
  • 3 Davis SE, Ide MS, Davis RJ. Green Chem. 2013; 15: 17
  • 4 Mancuso AJ, Huang S.-L, Swern D. J. Org. Chem. 1978; 43: 2480
  • 5 Sheldon RA, Arends IW. C. E, ten Brink G.-J, Dijksman A. Acc. Chem. Res. 2002; 35: 774
  • 6 De Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G. J. Org. Chem. 1997; 62: 6974
  • 7 De Luca L, Giacomelli G, Masala S, Porcheddu A. J. Org. Chem. 2003; 68: 4999
  • 8 Bolm C, Magnus AS, Hildebrand JP. Org. Lett. 2000; 2: 1173
  • 9 Miller RA, Hoerrner RS. Org. Lett. 2003; 5: 285
  • 10 Uyanik M, Ishihara K. Chem. Commun. 2009; 2086
    • 11a Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
    • 11b Meyer SD, Schreiber SL. J. Org. Chem. 1994; 59: 7549
    • 12a Frigerio M, Santagostino M, Sputore S, Palmisano G. J. Org. Chem. 1995; 60: 7272
    • 12b Corey EJ, Palani A. Tetrahedron Lett. 1995; 36: 3485
    • 12c Wirth T. Angew. Chem. Int. Ed. 2001; 40: 2812
  • 13 Tohma H, Maegawa T, Takizawa S, Kita Y. Adv. Synth. Catal. 2002; 344: 328
  • 14 Tohma H, Takizawa S, Maegawa T, Kita Y. Angew. Chem. Int. Ed. 2000; 39: 1306
  • 15 Takenaga N, Goto A, Yoshimura M, Fujioka H, Dohi T, Kita Y. Tetrahedron Lett. 2009; 50: 3227
  • 16 Ma X, Li Z, Liu F, Cao S, Rao H. Adv. Synth. Catal. 2014; 356: 1741
  • 17 Paraskevopoulou P, Petalidou E, Psaroudakis N, Stavropoulos P, Mertis K. Monatsh. Chem. 2005; 136: 2035
  • 18 Qian W, Jin E, Bao W, Zhang Y. Angew. Chem. Int. Ed. 2005; 44: 952
  • 19 Li Z, Tang ZH, Hu XX, Xia CG. Chem. Eur. J. 2005; 11: 1210
  • 20 Sakuratani K, Togo H. Synthesis 2003; 21
  • 21 Brünjes M, Sourkouni-Argirusi G, Kirschning A. Adv. Synth. Catal. 2003; 345: 635
  • 22 Iinuma M, Moriyama K, Togo H. Tetrahedron 2013; 69: 2961
  • 23 Ambreen N, Kumar R, Wirth T. Beilstein J. Org. Chem. 2013; 9: 1437
  • 24 Beejapur HA, Giacalone F, Noto R, Franchi P, Lucarini M, Gruttadauria M. ChemCatChem 2013; 5: 2991
  • 25 Beejapur HA, Campisciano V, Giacalone F, Gruttadauria M. Adv. Synth. Catal. 2015; 357: 51
  • 26 Gruttadauria M, Giacalone F, Noto R. Green Chem. 2013; 15: 2608
  • 27 Oxidation Procedure: Alcohol (1 mmol) was added to a mixture of BAIB (1.1 mmol) and bromide anions (0.2 mmol) in EtOAc (1.5 mL), and the mixture was stirred at room temperature for 24 h. The solvent was removed under reduced pressure and the crude product was checked by 1H NMR spectroscopy. In case of p-nitrobenzyl alcohol, anisole, and p-chlorobenzyl alcohol oxidations, the residue was purified by chromatography [PE to separate iodobenzene and PE–EtOAc (10:1) to separate the corresponding aldehyde].
  • 28 Mirafzal GA, Lozeva AM. Tetrahedron Lett. 1998; 39: 7263
  • 29 Leduc AB, Jamison TF. Org. Process Res. Dev. 2011; 16: 1082
  • 30 Li X.-Q, Zhang C. Synthesis 2009; 1163
  • 31 Reilly JJ, Duncan DJ, Wunz TP, Patsiga RA. J. Org. Chem. 1974; 39: 3291
  • 32 Ben-Daniel R, Alsters P, Neumann R. J. Org. Chem. 2001; 66: 8650
  • 33 Abramovich A, Toledo H, Pisarevsky E, Szpilman AM. Synlett 2012; 23: 2261