화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.20, No.1, 29-36, January, 2014
Polymer-supported IBX amide for mild and efficient oxidation reactions
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A facile simple preparation of polymer-supported IBX amide (IBX amide resin) from chloromethyl polystyrene resin was demonstrated. The IBX amide resins were prepared with high loading levels (~1.40 mmol g^(-1)). These reagents were found to be mild and efficient oxidants through oxidation of a range of alcohols, sulfides and phosphites to the corresponding carbonyl, sulfoxide and phosphate compounds without over-oxidation at room temperature. Consumed IBX amide resins were reused up to five times without significant loss of oxidative activity after repetitive regeneration.
  1. Tohma H, Kita Y, Advanced Synthesis and Catalysis., 346, 111 (2004)
  2. Zhdankin VV, Stang PJ, Chem. Rev., 102(7), 2523 (2002)
  3. Wirth T, Angewandte Chemie International Edition., 44, 3656 (2005)
  4. Nicolaou KC, Montagnon T, Baran PS, Zhong YL, J. Am. Chem. Soc., 124(10), 2245 (2002)
  5. Bernini R, Barontini M, Crisante F, Ginnasi M, Saladino R, Tetrahedron Letters., 50, 6519 (2009)
  6. Uyanik M, Ishihara K, Chemical Communications., 2806 (2009)
  7. Satam V, Harad A, Rajule R, Pati H, Tetrahedron Letters., 66, 7659 (2010)
  8. Yoon HJ, Choi JW, Jang HS, Cho JK, Byun JW, Lee YS, Synlett., 2, 165 (2011)
  9. Duschek A, Kirsch SF, Angewandte Chemie International Edition., 50, 1524 (2011)
  10. More JD, Finney NS, Organic Letters., 4, 3001 (2002)
  11. Surendra K, Krishnaveni NS, Reddy MA, Nageswar YVD, Rao KR, Journal of Organic Chemistry., 68, 2058 (2003)
  12. Liu Z, Chen ZC, Zheng QG, Organic Letters., 5, 3321 (2003)
  13. Zhdankin VV, Koposov AY, Netzel BC, Yashin NV, Rempel BP, Ferguson MJ, Tykwinski RR, Angewandte Chemie International Edition., 42, 2194 (2003)
  14. Zhdankin VV, Litvinov DN, Koposov AY, Luu T, Ferguson MJ, McDonald R, Tykwinski RR, Chemical Communications., 106 (2004)
  15. Zhdankin VV, Koposov AY, Litvinov DN, Ferguson MJ, McDonald R, Luu T, Tykwinski RRJ, Journal of Organic Chemistry., 70, 6484 (2005)
  16. Koposov AY, Litvinov DN, Zhdankin VV, Tetrahedron Letters., 45, 2719 (2004)
  17. Ladziata U, Koposov AY, Lo KY, Willging J, Nemykin VN, Zhdankin VV, Angewandte Chemie International Edition., 44, 7127 (2005)
  18. Koposov AY, Zhdankin VV, Synthesis., 22 (2005)
  19. Meprathu BV, Justik MW, Protasiewicz JD, Tetrahedron Letters., 46, 5187 (2005)
  20. Thottumkara AP, Vinod TK, Tetrahedron Letters., 43, 569 (2002)
  21. Ladziata U, Willging J, Zhdankin VV, Organic Letters., 8, 167 (2006)
  22. Bhattacharyya S, Combinatorial Chemistry and High Throughput Screening., 3, 65 (2000)
  23. Flynn DL, Crich JZ, Devraj RV, Hockerman SL, Parlow JJ, South MS, Woodard S, J. Am. Chem. Soc., 119(21), 4874 (1997)
  24. Booth RJ, Hodges JC, J. Am. Chem. Soc., 119(21), 4882 (1997)
  25. Fraile JM, Mayoral JA, Royo AJ, Salvador RV, Altava B, Luis SV, Burguete MI, Tetrahedron., 52, 9853 (1996)
  26. McNamara CA, Dixon MJ, Bradley M, Chem. Rev., 102(10), 3275 (2002)
  27. Mulbaier M, Giannis A, Angewandte Chemie International Edition., 40, 4393 (2001)
  28. Sorg G, Mengel A, Jung G, Rademann J, Angewandte Chemie International Edition., 40, 4395 (2001)
  29. Reed NN, Delgado M, Hereford K, Clapham B, Janda KD, Bioorganic and Medicinal Chemistry Letters., 12, 2047 (2002)
  30. Lei Z, Denecker C, Jegasothy S, Sherrington DC, Slater NKH, Sutherland AJ, Tetrahedron Letters., 44, 1635 (2003)
  31. Lei ZQ, Ma HC, Zhang Z, Yang YX, Reactive and Functional Polymers., 66, 840 (2006)
  32. Novabiochem catalog, 5, 397 (2004)
  33. Chung WJ, Kim DK, Lee YS, Tetrahedron Letters., 4, 9251 (2003)
  34. Kim DK, Chung WJ, Lee YS, Synlett., 279 (2005)
  35. Jang HS, Chung WJ, Lee YS, Tetrahedron Letters., 48, 3731 (2007)
  36. The preparation of IBX amide resins require the use of the precursor commercially available 2-iodobenzoic acid or 2-iodobenzoyl chloride to be attached to the resin followed by activation, whereas the conventional IBX resins need to be prepared using the precursor that are usually synthesized through multiple steps.
  37. Chung WJ, Kim DK, Lee YS, Synlett., 2175 (2005)
  38. Lecarpentier P, Crosignani S, Linclau B, Molecular Diversity., 9, 341 (2005)
  39. Arseniyadis S, Wagner A, Mioskowski C, Tetrahedron Letters., 43, 9717 (2002)
  40. Trost BM, Braslau R, Journal of Organic Chemistry., 53, 532 (1988)
  41. Dess DB, Martin JC, Journal of Organic Chemistry., 48, 4155 (1983)
  42. Dess BD, Martin JC, Journal of the American Chemical Society., 113, 7277 (1991)
  43. Frigerio M, Santagostino M, Sputore S, Journal of Organic Chemistry., 64, 4537 (1999)
  44. Nicolaou KC, Baran PS, Zhong YL, J. Am. Chem. Soc., 123(13), 3183 (2001)
  45. Moriarty RM, Vaid RK, Ravikumar VT, Vaid BK, Hopkins TE, Tetrahedron Letters., 44, 1603 (1988)
  46. Ochiai M, Miyamoto K, Shiro M, Ozawa T, Yamaguchi K, J. Am. Chem. Soc., 125(43), 13006 (2003)
  47. Shukla VG, Salgaonkar PD, Akamanchi KG, Journal of Organic Chemistry., 68, 5422 (2003)
  48. Soulard M, Block F, Hatterer AJ, Journal of the Chemical Society, Dalton Transactions., 2300 (1981)