Selective oxidation of aromatic primary alcohols to aldehydes using molybdenum acetylide oxo-peroxo complex as catalyst

Tetrahedron Letters

Volumn 50, Issue 24, 2009, Pages 2885-2888

  Biradar, Ankush V ^a   Dongare, Mohan K ^a   Umbarkar, Shubhangi B ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Homogenous catalyst; Hydrogen peroxide; Molybdenum complex; Oxidation; Oxo peroxo; Primary aromatic alcohol

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AROMATIC PRIMARY ALCOHOL DERIVATIVE; CYCLOPENTADIENYL MOLYBDENUM ACETYLIDE COMPLEX; HYDROGEN PEROXIDE; MOLYBDENUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; OXIDATION;

EID: 65249130648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.178     Document Type: Article

References (54)

1. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (1992), Wiley, New York
2. Sheldon R.A., and Kochi J.K. Metal-Catalyzed Oxidation of Organic Compounds (1981), Academic Press, New York
3. Brink G.T., Arends I.W.C.E., and Sheldon R.A. Science 47 (2000) 1636
4. Enache D.I., Edwards J.K., Landon P., Solsona-Espriu B., Carley A.F., Herzing A.A., Watanabe M., Kiely C.J., Knight D.W., and Hutchings G.J. Science 311 (2006) 362
5. Beller M., and Bolm C. Transition Metals for Organic Synthesis. 2nd ed. (2004), Verlag GmbH & Co. KGaA, Weinheim, Germany
6. Pillai U.R., and Sahle-Demessie E. Appl. Catal. Gen 245 (2003) 103
7. Hudlicky M. Oxidations in Organic Chemistry (1990), American Chemical Society, Washington, DC
8. Menger F.M., and Lee C. Tetrahedron Lett. 22 (1981) 1655
9. Lee C.K., Koo B.S., Lee Y.S., Cho H., and Lee K.K.-J. Bull. Korean Chem. Soc. 23 (2002) 1667
10. For a general review on chromium oxidations, see for example:. Cainelli G., and Cardillo G. Chromium Oxidants in Organic Chemistry (1984), Springer, Berlin
11. Ley S.V., and Madin A. In: Trost B.M., Fleming I., and Ley S.V. (Eds). Comprehensive Organic Synthesis Vol. 7 (1991), Pergamon, Oxford 251
12. Seddon K.R., and Stark A. Green Chem. 4 (2002) 119
13. Ganchegui B., Bouquillon S., Henin F., and Muzart J. Tetrahedron Lett 43 (2002) 6641
14. Muzart J. Tetrahedron 59 (2003) 5789
15. Ganchegui B., Bouquillon S., Henin F., and Muzart J. J. Mol. Catal. A: Chem. 214 (2004) 65
16. Hardacre C., Mullan E.A., Rooney D.W., and Thompson J.M. J. Catal. 232 (2005) 355
17. Nishimura T., Onoue T., Ohe K., and Uemura S. Tetrahedron Lett. 39 (1998) 6011
18. Nagata H., and Ogasawara K. Tetrahedron Lett. 40 (1999) 6617
19. ten Brink G.-J., Arends I.W.C.E., and Sheldon R.A. Science 287 (2000) 1636
20. Besson M., and Callezot P. Catal. Today 57 (2000) 127
21. Nishimura T., Kakiuchi N., Inoue M., and Uemura S. Chem. Commun. (2000) 1245
22. Kakiuchi N., Maeda Y., Nishimura T., and Uemura S. J. Org. Chem. 66 (2001) 6620
23. Peterson K.P., and Larock R.C. J. Org. Chem. 63 (1998) 3185
24. Wolfson A., Wuyts S., De V.D., Vankelecom I.F.J., and Jacobs P.A. Tetrahedron Lett. 43 (2002) 8107
25. Tang W.M., and Li C.J. Acta Chim. Sini. 62 (2004) 742
26. Roberto F.D.S., Jairton D., and Jeane E.D. J. Braz. Chem. Soc. 17 (2006) 48
27. Shi F., Tse M., and Beller M. Chem. Asian J. 2 (2007) 411
28. Chhikara B.S., Tehlan S., and Kumar A. Synlett (2005) 63
29. Chhikara B.S., Chandra R., and Tandon V. J. Catal. 230 (2005) 436
30. Bianchini G., Crucianelli M., de Angelis F., Neri V., and Saladino R. Tetrahedron Lett. 46 (2005) 2427
31. Kumar A., Jain N., and Chauhan S.M.S. Synlett (2007) 411
32. Gamez P., Arends I.W.C.E., Sheldon R.A., and Reedijk J. Adv. Synth. Catal. 346 (2004) 805
33. Jiang N., and Ragauskas A.J. J. Org. Chem. 71 (2006) 7087
34. Han H., Zhang S., Hou H., Fan Y., and Zhu Y. Eur. J. Inorg. Chem. (2006) 1594
35. Marti{dotless}n S.E., and Suarez D.F. Tetrahedron Lett. 43 (2002) 4475
36. Veitch G.V., Boyer A., and Ley S.V. Angew. Chem., Int. Ed. 47 (2008) 9402
37. Yasuda K., and Ley S.V. J. Chem. Soc., Perkin Trans. 1 (2002) 1024
38. Khanbabaee K.K. Ann. Chem. (1993) 905
39. Krohn K., Bruggmann K., Doring D., and Jones P.G. Chem. Ber. 125 (1992) 2439
40. Krohn K., Rieger H., and Bruggmann K. Synthesis (1990) 1141
41. Patnaik P. Handbook of Inorganic Chemicals (2003), McGraw Hill
42. Manyar H.G., Chaure G.S., and Kumar A. J. Mol. Catal. A 243 (2006) 244
43. Maiti S.K., Abdul Malik K.M., and Bhattacharyya R. Inorg. Chem. Commun. 7 (2004) 823
44. Abrantes M., Santos A.M., Mink J., Kuhn F.E., and Romao C.C. Organometallics 22 (2003) 2112
45. Grivani G., Tangestaninejad S., Habibi M.H., and Mirkhani V. Catal. Commun. 6 (2005) 375
46. Martins A.M., Romao C.C., Abrantes M.M., Azevedo C., Cui J., Dias A.R., Duarte M.T., Lemos M.A., Lourenco T., and Poli R. Organometallics 24 (2005) 2582
47. Biradar A.V., Sathe B.R., Dongare M.K., and Umbarkar S.B. J. Mol. Catal. A 285 (2008) 111
48. Biradar A.V., Kotbagi T.V., Dongare M.K., and Umbarkar S.B. Tetrahedron Lett. 49 (2008) 3616
49. 13C); 92.93 (Cp), 87.85. 126.01, 127.0, 129.39, 130.8, 130.87 (C{triple bond, long}CPh); 222.4, 238.78 (CO)
50. 2 (10.02 g, 0.1 mol) were added to a two-necked 50 mL round-bottomed flask. The reaction mixture was vigorously stirred (750 rpm) at 80 °C for 8 h. After the reaction, a two-layer mixture was obtained (organic phase/water phase), The reaction was monitored using GC (Agilent 6890 Gas Chromatograph equipped with a HP-5 dimethyl polysiloxane (60 m length, 0.25 mm internal diameter, 0.25 μm film thickness) with flame ionization detector. Products were confirmed using GC-MS (Model GC Agilent 6890 N with HP5 MS 30 m capillary column, MS Agilent 5973 Network MSD.
51. Minisci F., Punta C., Recupero F., Fontana F., and Pedulli G.F. Chem. Commun. (2002) 688
52. Cecchetto A., Fontana F., Minisci F., and Recupero F. Tetrahedron Lett. 42 (2001) 6651
53. Hida T., and Nogusa H. Tetrahedron 65 (2009) 270
54. Maiti S.K., Banerjee S., Mukharjee A.K., Malik K.M.A., and Bhattacharyya R. New. J. Chem. 29 (2005) 554