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NaBrO3/bmim[HSO4]: a versatile system for the selective oxidation of 1,2-diols, α-hydroxyketones, and alcohols

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Abstract

Sodium bromate with bmim[HSO4] has been found to be an excellent oxidizing agent in aqueous medium. NaBrO3:bmim[HSO4] oxidized 1,2-diols, α-hydroxyketones, and alcohols to the corresponding carbonyl compounds in excellent yields. This method offers advantages such as low cost reagents, aqueous reaction conditions, moderate temperatures and short reaction times and hence environmentally benign reaction. Moreover, the ionic liquid bmim[HSO4] could be recycled for at least three times without loss of significant activity.

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References

  1. Richardson WH (1965) In: Wiberg KB (ed) Oxidation in Organic Chemistry, Part A, Ch. IV. Academic Press, New York

    Google Scholar 

  2. Ojha LR, Kudugunti S, Maddukuri PP, Kommareddy A, Gunna MR, Dokuparthi P, Gottam HB, Botha KK, Parapati DR, Vinod TK (2009) Synlett 1:117

    Google Scholar 

  3. Yusubov MS, Zagulyaeva AA, Zhdankin VV (2009) Chem Eur J 15:11091

    Article  CAS  Google Scholar 

  4. Stang PJ, Zhdankin VV (1996) Chem Rev 96:1123

    Article  CAS  Google Scholar 

  5. Shim WG, Jung SC, Seo SG, Kim SC (2011) Catal Today 164:500

    Article  CAS  Google Scholar 

  6. Khurana JM, Nand B (2010) Can J Chem 88:906

    Article  CAS  Google Scholar 

  7. Khurana JM, Agrawal A, Kumar S (2009) J Braz Chem Soc 20:1256

    Article  CAS  Google Scholar 

  8. Khurana JM, Kandpal BM (2003) Tetrahedron Lett 44:4909

    Article  CAS  Google Scholar 

  9. Khurana JM, Kandpal BM, Chauhan YK (2003) Phosphorus Sulfur Silicon Relat Elem 178:1369

    Article  CAS  Google Scholar 

  10. Kikuchi D, Sakaguchi S, Ishii Y (1998) J Org Chem 63:6023

    Article  CAS  Google Scholar 

  11. Kajigaeshi S, Nakagawa T, Nagasaki N, Yamasaki H, Fujusaki S (1986) Bull Chem Soc Jpn 59:747

    Article  CAS  Google Scholar 

  12. Tomioka H, Oshima K, Nozaki H (1982) Tetrahedron Lett 23:539

    Article  CAS  Google Scholar 

  13. Wang YL, Zhao YW, Wang XX, Duan ZF (2002) Synth Commun 32:1781

    Article  CAS  Google Scholar 

  14. Metsger L, Bittner S (2000) Tetrahedron 56:1905

    Article  CAS  Google Scholar 

  15. Shaabani A, Bazgir A, Abdoli M (2002) Synth Commun 32:675

    Article  CAS  Google Scholar 

  16. Shaabani A, Bazgir A, Soleimani K, Salehi P (2003) Synth Commun 33:2935

    Article  CAS  Google Scholar 

  17. Shaabani A, Soleimani K, Bazgir A (2004) Synth Commun 34:3303

    Article  CAS  Google Scholar 

  18. Shaabani A, Lee DG (2003) Sulfur Lett 26:43

    Article  CAS  Google Scholar 

  19. Wasserschield P, Keim W (2000) Angew Chem Int Ed 39:3772

    Article  Google Scholar 

  20. Hajipour AR, Khazdooz L, Ruoho AE (2008) Catal Commun 9:89

    Article  CAS  Google Scholar 

  21. Greaves TL, Drummond CJ (2008) Chem Rev 108:206

    Article  CAS  Google Scholar 

  22. Guo S, Du Z, Zhang S, Li D, Li Z, Deng Y (2006) Green Chem 8:296

    Article  CAS  Google Scholar 

  23. Muzart J (2006) Adv Synth Catal 348:275

    Article  CAS  Google Scholar 

  24. Shaabani A, Farhangi E, Rahmati A (2008) Monatsh Chem 139:905

    Article  CAS  Google Scholar 

  25. Safari J, Arani NM, Isfahani AR (2011) Asian J Chem 23:495

    CAS  Google Scholar 

  26. Kulkarni GC, Karmarkar SN, Kelkar SL, Murzban WS (1988) Tetrahedron 44:5189

    Article  CAS  Google Scholar 

  27. Shimakawa Y, Morikawa T, Sakaguchi S (2010) Tetrahedron Lett 51:1786

    Article  CAS  Google Scholar 

  28. Rose CA, Gundala S, Cannon SJ, Zeitler K (2011) Synthesis 190

  29. Wang X, Zhang Y (2003) Tetrahedron 59:4201

    Article  CAS  Google Scholar 

  30. Jaunin R, Sechaud G (1956) Helv Chim Acta 39:1257

    Article  CAS  Google Scholar 

  31. Chen CT, Kao JQ, Salunke SB, Kin YH (2011) Org Lett 13:26

    Article  CAS  Google Scholar 

  32. Futami Y, Nishino H, Kurosawa K (1989) Bull Chem Soc Jpn 62:3182

    Article  CAS  Google Scholar 

  33. Gregoire B, Carre MC, Caubere P (1986) J Org Chem 51:1419

    Article  CAS  Google Scholar 

  34. Jing X, Pan X, Li Z, Shi Y, Yan C (2009) Synth Commun 39:492

    Article  CAS  Google Scholar 

  35. Shine HJ, Rangappa P, Marx JN, Shelly DC, Ould-Ely T, Whitmire KH (2005) J Org Chem 70:3877

    Article  CAS  Google Scholar 

  36. Syper L (1987) Tetrahedron 43:2853

    Article  CAS  Google Scholar 

  37. Sharghi H, Jokar M, Mahboubeh D, Mohammad M, Khalifeh R (2010) Adv Synth Catal 352:3031

    Article  CAS  Google Scholar 

  38. Chen JY, Chen SJ, Tang YJ, Mou CY, Tsai FY (2009) J Mol Catal A: Chem 307:88

    Article  CAS  Google Scholar 

  39. Marvel CS, Nichols V (1941) J Org Chem 6:296

    Article  CAS  Google Scholar 

  40. Cunningham A, Mokal-Parekh V, Wilson C, Woodward S (2004) Org Biomol Chem 2:741

    Article  CAS  Google Scholar 

  41. Paakkonen S, Pursiainen J, Lajunen M (2010) Tetrahedron Lett 51:6695

    Article  CAS  Google Scholar 

  42. Tucker-Schwartz AK, Garrell RL (2010) Chem Eur J 16:12718

    Article  CAS  Google Scholar 

  43. Ali MH, Greene S, Wiggin CJ, Khan S (2006) Synth Commun 36:1761

    Article  CAS  Google Scholar 

  44. Maddani M, Prabhu KR (2008) Tetrahedron Lett 49:4526

    Article  CAS  Google Scholar 

  45. Xi B, Nevalainen V (2006) Tetrahedron Lett 47:7133

    Article  CAS  Google Scholar 

  46. Iinuma M, Moriyama K (2013) Tetrahedron 69:2961

    Article  CAS  Google Scholar 

  47. Rolfe A, Probst DA, Volp KA, Omar I, Flynn DL, Hanson PR (2008) J Org Chem 73:8785

    Article  CAS  Google Scholar 

  48. Akkilagunta VK, Reddy VP, Kakulapati RR (2010) Synlett 17:2571

    Google Scholar 

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Acknowledgments

AL thanks University of Delhi for the award of University Teaching Assistantship and AC thanks C.S.I.R., New Delhi, India for the grant of Senior Research Fellowship.

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Correspondence to Jitender M. Khurana.

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Khurana, J.M., Lumb, A. & Chaudhary, A. NaBrO3/bmim[HSO4]: a versatile system for the selective oxidation of 1,2-diols, α-hydroxyketones, and alcohols. Monatsh Chem 148, 381–386 (2017). https://doi.org/10.1007/s00706-016-1749-z

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  • DOI: https://doi.org/10.1007/s00706-016-1749-z

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