Download PDF
Synlett 2011(4): 555-558  
DOI: 10.1055/s-0030-1259538
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Oxidation of Activated Alcohols by the Combination of H2O2, AcOH and NaBr: An Efficient Metal-Free Alternative

Xingyi Qi*, Jing Wang, Liwei Zheng, Lin Qi
School of Chemistry and Environment, Beijing University of Aeronautics and Astronautics, Beijing 100191, P. R. of China
Fax: +86(10)82313981; e-Mail: qixy@buaa.edu.cn;
Further Information

Publication History

Received 29 October 2010
Publication Date:
08 February 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

The ternary H2O2-AcOH-NaBr combination has been found to be extremely effective for the oxidation of benzyl alcohol and its derivatives. Comparative studies indicated that the addition of NaBr offered significant improvement in product yields and selectivity towards aldehyde formation.

Key words

alcohols - selective oxidation - aldehydes - ketones

    References

  • 1 Sheldon RA. Kochi JK. Metal-Catalysed Oxidations of Organic Compounds   Sheldon RA. Academic Press; New York: 1981.  p.350-357  
    Google Scholar
  • 2 Sheldon RA. Arends IWCE. Dijkman A. Catal. Today.  2000,  57:  157 
    CrossrefGoogle Scholar
  • 3a Matsumoto M. Ito S. J. Chem. Soc., Chem. Commun.  1981,  907 
    Google Scholar
  • 3b Matsumoto M. Watanabe N. J. Org. Chem.  1984,  49:  3435 
    Google Scholar
  • 3c Tashiro A. Mitsuishi A. Irie R. Katsuki T. Synlett  2003,  1868 
    Google Scholar
  • 3d Tang R. Diamond SE. Neary N. Mares F. J. Chem. Soc., Chem. Commun.  1978,  562 
    Google Scholar
  • 3e Bilgrien C. Davis S. Drago RS. J. Am. Chem. Soc.  1987,  109:  3786 
    Google Scholar
  • 4a Brink G. Arends IWCE. Sheldon RA. Science  2000,  287:  1636 
    Google Scholar
  • 4b Steinhoff BA. Stahl SS. Org. Lett.  2002,  4:  4179 
    Google Scholar
  • 4c Kwon MS. Kim N. Park CM. Lee JS. Kang KY. Park J. Org. Lett.  2005,  7:  1077 
    Google Scholar
  • 4d Batt F. Bourcet E. Kassab Y. Fache F. Synlett  2007,  1869 
    Google Scholar
  • 5 Chen JD. Lempers HEB. Sheldon RA. J. Chem. Soc., Faraday Trans.  1996,  92:  1807 
    CrossrefGoogle Scholar
  • 6a Marko IE. Giles PR. Tsukazaki M. Brown SM. Urch CJ. Science  1996,  274:  2044 
    Google Scholar
  • 6b Aoyama T. Sonoda T. Yamauchi M. Toriyama K. Anzai M. Ando A. Shioiri T. Synlett  1998,  35 
    Google Scholar
  • 6c Kamijo S. Amaoka Y. Inoue M. Synthesis  2010,  2475 
    Google Scholar
  • 7 Iwahama T. Sakaguchi S. Nishiyama Y. Ishii Y. Tetrahedron Lett.  1995,  36:  6923 
    CrossrefGoogle Scholar
  • 8a Son Y. Makwana VD. Howelll AR. Suib SL. Angew. Chem. Int. Ed.  2001,  40:  4280 
    Google Scholar
  • 8b Pande S. Saha A. Jana S. Sarkar S. Basu M. Pradhan M. Sinha AK. Saha S. Pal A. Pal T. Org. Lett.  2008,  10:  5179 
    Google Scholar
  • 9 Hou W. Dehm NA. Scott RWJ. J. Catal.  2008,  253:  22 
    CrossrefGoogle Scholar
  • 10 Friedrich HB. Khan F. Singh N. van Stadenb M. Synlett  2001,  869 
    Google Scholar
  • 11 Enache DI. Edwards JK. Landon P. Solsona-Espriu B. Carley AF. Herzing AA. Watanabe M. Kiely CJ. Knight DW. Hutchings GJ. Science  2006,  311:  362 
    CrossrefGoogle Scholar
  • 12a van der Pol AJHP. van Hooff JHC. Appl. Catal. A: Gen.  1993,  106:  97 
    Google Scholar
  • 12b Maspero F. Romano FU. J. Catal.  1994,  146:  476 
    Google Scholar
  • 13 Ratnasamy P. Kumar R. Stud. Surf. Sci. Catal.  1995,  97:  367 
    Google Scholar
  • 14 Jappar N. Xia A. Tatsumi T. J. Catal.  1998,  180:  132 
    CrossrefGoogle Scholar
  • 15a Haanepen MJ. Elemans-Mehring AM. van Hooff JHC. Appl. Catal. A: Gen.  1997,  152:  203 
    Google Scholar
  • 15b Chen JD. Haanepen MJ. van Hooff JHC. Sheldon RA. Stud. Surf. Sci. Catal.  1994,  84:  973 
    Google Scholar
  • 16 Pillai UR. Sahle-Demessie E. Appl. Catal. A: Gen.  2003,  245:  103 
    CrossrefGoogle Scholar
  • 17a Wang X. Wu G. Li J. Zhaoa N. Wei W. Suna Y. J. Mol. Catal. A: Chem.  2007,  276:  86 
    Google Scholar
  • 17b Bansala VK. Thankachan PP. Prasad R. Appl. Catal. A: Gen.  2010,  381:  8 
    Google Scholar
  • 18a Dakka J. Sasson Y. Bull. Soc. Chim. Fr.  1988,  4:  756 
    Google Scholar
  • 18b Espenson JH. Pestovsky O. Huston P. Staudt S.
    J. Am. Chem. Soc.  1994,  116:  2869 
    Google Scholar
  • 18c Amati A. Dosualdo G. Zhao LH. Bravo A. Fontana F. Minisci F. Bjorsvik HR. Org. Process Res. Dev.  1998,  2:  261 
    Google Scholar
  • 19a Espenson JH. Zhu Z. Zauche TH. J. Org. Chem.  1999,  64:  1191 
    Google Scholar
  • 19b Palou J. Chem. Soc. Rev.  1994,  23:  357 
    Google Scholar
  • 19c Stewart R. Oxidation Mechanisms: Applications to Organic Chemistry   W. A. Benjamin Inc.; New York: 1964.  p.18-26  
    Google Scholar
  • 19d Farkas L. Perlmutter B. Schachter O. J. Am. Chem. Soc.  1949,  71:  2829 
    Google Scholar
  • 19e Uyanik M. Fukatsu R. Ishihara R. Chem. Asian J.  2010,  5:  456 
    Google Scholar