Download PDF
Synlett 2012; 23(9): 1397-1401
DOI: 10.1055/s-0031-1290980
letter
© Georg Thieme Verlag Stuttgart · New York

Novel [4-Hydroxy-TEMPO + NaCl]/SiO2 as a Reusable Catalyst for Aerobic Oxidation of Alcohols to Carbonyls

Naoya Tamura
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan, Fax: +81(3)32590818   Email: aoyama.tadashi@nihon-u.ac.jp
,
Tadashi Aoyama*
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan, Fax: +81(3)32590818   Email: aoyama.tadashi@nihon-u.ac.jp
b   The Center for Creative Materials Research, Research Institute of Science and Technology, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan
,
Toshio Takido
a   Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan, Fax: +81(3)32590818   Email: aoyama.tadashi@nihon-u.ac.jp
,
Mitsuo Kodomari
c   Department of Bioscience and Engineering, Shibaura Institute of Technology, Fukasaku, Minuma-ku, Saitama 337-8570, Japan
› Author Affiliations
Further Information

Publication History

Received: 17 January 2012

Accepted after revision: 22 March 2012

Publication Date:
14 May 2012 (online)

    Permissions and Reprints All articles of this category


Abstract

A convenient method for the preparation of [4-hydroxy-TEMPO + NaCl]/SiO2 was developed. And [4-hydroxy-TEMPO + NaCl]/SiO2 with Fe(NO3)3·9H2O was used for an aerobic oxidation of alcohols to carbonyls under mild reaction conditions. Alcohols were converted to the corresponding carbonyls in good to excellent yields. [4-Hydroxy-TEMPO + NaCl]/SiO2 can be easily separated from the reaction mixture by filtration and reused at least six times.

Key words

alcohols - TEMPO - oxidation - supported catalyst - ketones
 

  • References and Notes

  • 1 Corey EJ, Suggs JW. Tetrahedron Lett. 1975; 16: 2647
    Crossref
    • 2a Omura K, Swern D. Tetrahedron 1978; 34: 1651
      Crossref
    • 2b Mermet-Mouttet M, Gabriel K, Heissler D. Tetrahedron Lett. 1999; 40: 843
      Crossref
    • 2c Silva CB, Benkouider A, Pale P. Tetrahedron Lett. 2000; 41: 3077
      Crossref
    • 2d Suenaga K, Araki K, Sengoku T, Uemura D. Org. Lett. 2001; 3: 527
      CrossrefPubMed
    • 2e Kaiser F, Schmalz H. Tetrahedron 2003; 59: 7345
      Crossref
    • 2f Lane JW, Chen Y, Williams RM. J. Am. Chem. Soc. 2005; 127: 12684
      Crossref
    • 2g ElMarrouni A, Fukuda A, Heras M, Arseniyadis S, Cossy J. J. Org. Chem. 2010; 75: 8478
      Crossref
    • 3a Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
      Crossref
    • 3b Olpp T, Bruckner R. Angew. Chem. Int. Ed. 2006; 45: 4023
    • 3c Rein C, Demel P, Outten RA, Netscher T, Breit B. Angew. Chem. Int. Ed. 2007; 46: 8670
      Crossref
    • 3d Hangyou M, Ishiyama H, Takahashi Y, Kobayashi J. Org. Lett. 2009; 11: 5046
      Crossref
    • 3e Srinivas B, Sridhar R, Rao KR. Tetrahedron 2010; 66: 8527
      Crossref
    • 3f Crimmins MT, Haley MW, O’Bryan EA. Org. Lett. 2011; 13: 4712
      Crossref
  • 4 Cella JA, Kelley JA, Kenehan EF. J. Org. Chem. 1975; 40: 1860
    Crossref
  • 5 Ganem B. J. Org. Chem. 1975; 40: 1998
    Crossref
  • 6 Anelli PL, Biffi C, Montanari F, Quici S. J. Org. Chem. 1987; 52: 2559
    Crossref
  • 7 Mico AD, Margarita R, Parlanti L, Vescovi A, Piancatelli G. J. Org. Chem. 1997; 62: 6974
    Crossref
  • 8 Semmelhack MF, Schmid CR, Cortes DA, Chou CS. J. Am. Chem. Soc. 1984; 106: 3374
    Crossref
  • 9 Wang X, Liang X. Chin. J. Catal. 2008; 29: 935
    Crossref
  • 10 Yin W, Chu C, Lu Q, Tao J, Liang X, Liu R. Adv. Synth. Catal. 2010; 352: 113
    Crossref
  • 12 Fey T, Fischer H, Bachmann S, Albert K, Bolm C. J. Org. Chem. 2001; 66: 8154
    Crossref
  • 13 Benaglia M, Puglisi A, Holczknecht O, Quici S, Pozzi G. Tetrahedron 2005; 61: 12058
    Crossref
  • 14 Fall A, Sene M, Gaye M, Gomez G, Fall Y. Tetrahedron Lett. 2010; 51: 4501
    Crossref
  • 15 Karimi B, Farhangi E. Chem. Eur. J. 2011; 17: 6056
    Crossref
    • 16a Tucker-Schwartz AK, Garrell RL. Chem. Eur. J. 2010; 16: 12718
      Crossref
    • 16b Karimi B, Badreh E. Org. Biomol. Chem. 2011; 9: 4194
      Crossref
  • 17 Ma S, Liu J, Li S, Chen B, Cheng J, Kuang J, Liu Y, Wan B, Wang Y, Ye J, Yu Q, Yuan W, Yub S. Adv. Synth. Catal. 2011; 353: 1005
    Crossref
  • 18 The content of water was estimated by weight difference between [4-hydroxy-TEMPO + NaCl]/SiO2 and [4-hydroxy-TEMPO + NaCl]/SiO2 which was dried at 160 °C under reduced pressure (8 mmHg) for 3 h
  • 19 Aerobic Oxidation of Alcohols A mixture of alcohols (2.0 mmol), Fe(NO3)3·9H2O (5–8 mol%) and [4-hydroxy-TEMPO + NaCl]/SiO2 [(0.1 + 0.1) mmol/g, 1.0 g] was stirred in DCE (5 mL) under air (1 atm) at r.t., and then the used supported reagent were removed by filtration. Product yield was determined by GLC analysis using n-dodecane as internal standard