Download PDF
Synthesis 2010(23): 3974-3976  
DOI: 10.1055/s-0030-1258278
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A 4-MeO-TEMPO, PEG-NO2 and HCl Catalytic System for Highly Efficient Aerobic Oxidation of Alcohols

Jianwei Taoa, Qiongqiong Lua, Changhu Chu*a, Renhua Liu*a, Xinmiao Liang*a,b
a East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
Fax: +86(21)64250627; e-Mail: chuch@ecust.edu.cn; e-Mail: liurh@ecust.edu.cn;
b Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China
Fax: +86(411)84379539; e-Mail: liangxm@dicp.ac.cn;
Further Information

Publication History

Received 9 August 2010
Publication Date:
30 September 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

A combination of 4-MeO-TEMPO/PEG-NO2/HCl for catalytic aerobic oxidation of alcohol is described. A wide range of alcohols was efficiently oxidized to the corresponding carbonyl compounds by using this oxidation system and the turnover number (TON) for benzyl alcohol oxidation reached up to 56000.

Key words

alcohol oxidation - PEG-NO2 - 4-MeO-TEMPO - dioxygen - efficient

    References

  • 1a Gallezot P. Catal. Today  1997,  37:  405 
    Google Scholar
  • 1b Thomas JM. Raja R. Catal. Today  2006,  117:  22 
    Google Scholar
  • 1c Lenoir D. Angew. Chem. Int. Ed.  2006,  45:  3206 
    Google Scholar
  • 2a Collins TJ. Acc. Chem. Res.  1994,  27:  279 
    Google Scholar
  • 2b Hill CL. Weinstock IA. Nature  1997,  388:  332 
    Google Scholar
  • 2c Weinstock IA. Barbuzzi EMG. Wemple MW. Cowan JJ. Reiner RS. Sonnen DM. Heintz RA. Bond JS. Hill CL. Nature  2001,  414:  191 
    Google Scholar
  • 2d Hill CL. Angew. Chem. Int. Ed.  2004,  43:  402 
    Google Scholar
  • 2e Stahl SS. Angew. Chem. Int. Ed.  2004,  43:  3400 
    Google Scholar
  • 3a Grinstaff MW. Hill MG. Labinger JA. Gray HB. Science  1994,  264:  1311 
    Google Scholar
  • 3b Sorokin A. Seris JL. Meunier B. Science  1995,  268:  1163 
    Google Scholar
  • 3c Horwitz CP. Fooksman DR. Vuocolo LD. Gordon-Wylie SW. Cox NJ. Collins TJ. J. Am. Chem. Soc.  1998,  120:  4867 
    Google Scholar
  • 3d Gupta SS. Stadler M. Noser CA. Ghosh A. Steinhoff B. Lenoir D. Horwitz CP. Schramm KW. Collins TJ. Science  2002,  296:  326 
    Google Scholar
  • 3e Chang CK. Ebina F. J. Chem. Soc., Chem. Commun.  1981,  778 
    Google Scholar
  • 4a Dijksman A. Marino-Gonzalez A. Mairata i payeras A. Arends IWCE. Sheldon RA. J. Am. Chem. Soc.  2001,  123:  6826 
    Google Scholar
  • 4b Zhang M. Chen C. Ma W. Zhao J. Angew. Chem. Int. Ed.  2008,  47:  9730 
    Google Scholar
  • 4c He X. Shen Z. Mo W. Sun N. Hu B. Hu X. Adv. Synth. Catal.  2009,  351:  89 
    Google Scholar
  • 4d Figiel PJ. Leskelä M. Repo T. Adv. Synth. Catal.  2007,  349:  1173 
    Google Scholar
  • 4e Wang N. Liu R. Chen J. Liang X. Chem. Commun.  2005,  5322 
    Google Scholar
  • 4f Gamez P. Arends IWCE. Reedijk J. Sheldon RA. Chem. Commun.  2003,  2414 
    Google Scholar
  • 5a Fey T. Fischer H. Bachmann S. Albert K. Bolm C. J. Org. Chem.  2001,  66:  8154 
    Google Scholar
  • 5b Ciriminna R. Bolm C. Fey T. Pagliaro M. Adv. Synth. Catal.  2002,  344:  159 
    Google Scholar
  • 5c Brunel D. Fajula F. Nagy JB. Deroide B. Verhoef MJ. Veum L. Peters JA. van Bekkum H. Appl. Catal., A  2001,  213:  73 
    Google Scholar
  • 5d Karimi B. Biglari A. Clark JH. Budarin V. Angew. Chem. Int. Ed.  2007,  46:  7210 
    Google Scholar
  • 5e Pozzi G. Cavazzini M. Quici S. Benaglia M. Dell’Anna G. Org. Lett.  2004,  6:  441 
    Google Scholar
  • 6 Liu R. Liang X. Dong C. Hu X. J. Am. Chem. Soc.  2004,  126:  4112 
    CrossrefPubMedGoogle Scholar
  • 7a Liu R. Dong C. Liang X. Wang X. Hu X. J. Org. Chem.  2005,  70:  729 
    Google Scholar
  • 7b Liang X. Fu D. Liu R. Zhang Q. Zhang TY. Hu X. Angew. Chem. Int. Ed.  2005,  44:  5520 
    Google Scholar
  • 7c Wang X. Liu R. Jin Y. Liang X. Chem. Eur. J.  2008,  14:  2679 
    Google Scholar
  • 7d Dobbs AP. Penny MJ. Jones P. Tetrahedron Lett.  2008,  49:  6955 
    Google Scholar
  • 7e Kloth K. Brünjes M. Kunst E. Joge T. Gallier F. Adibekian A. Kirschning A. Adv. Synth. Catal.  2005,  347:  1423 
    Google Scholar
  • 7f Xie Y. Mo W. Xu D. Shen Z. Sun N. Hu B. Hu X. J. Org. Chem.  2007,  72:  4288 
    Google Scholar
  • 7g Yang G. Zhu W. Zhang P. Xue H. Wang W. Tian J. Song M. Adv. Synth. Catal.  2008,  350:  542 
    Google Scholar
  • 7h Huang J. Li S. Wang Y. Tetrahedron Lett.  2006,  47:  5637 
    Google Scholar
  • 7i Lei M. Hu R. Wang Y. Tetrahedron  2006,  62:  8928 
    Google Scholar
  • 7j Yin W. Chu C. Lu Q. Tao J. Liang X. Liu R. Adv. Synth. Catal.  2010,  352:  113 
    Google Scholar
  • 8 Qiao R. Zhang Y. Hui X. Xu P. Zhang Z. Wang X. Wang Y. Green Chem.  2001,  3:  186 
    CrossrefGoogle Scholar