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Synthesis, structural characterization and alcohol oxidation activity of a new mononuclear manganese(II) complex

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Abstract

A manganese(II) complex of 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz) has been synthesized and characterized by single-crystal X-ray diffraction, elemental analyses, IR, and UV–Vis spectroscopic techniques. Oxidation of alcohols to their corresponding aldehydes and ketones was conducted by this catalyst using oxone (2KHSO5·KHSO4·K2SO4) as an oxidant under biphasic reaction conditions (CH2Cl2/H2O) and tetra-n-butylammonium bromide as phase transfer agent under air at room temperature. Easy preparation, mild reaction conditions, high yields of the products, short reaction times, no further oxidation to the corresponding carboxylic acids, high selectivity and inexpensive reagents make this catalytic system a useful oxidation method for aliphatic and benzylic alcohols.

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References

  1. Bäckvall JE (ed) (2004) Modern oxidation methods. Wiley-VCH, Weinheim

  2. Roberts SM (2007) Catalysts for fine chemical synthesis. Wiley-VCH, Weinheim

  3. Olason G, Sherrington DC (1999) React Funct Polym 42:163

    Article  CAS  Google Scholar 

  4. Davies JA, Watson PL, Liebman JF, A. Greenberg A (eds) (1990) Selective hydrocarbon oxidation, principles and progress. VCH, New York

  5. Simadi LI (ed) (1991) Dioxygen activation and homogeneous catalytic oxidation. Elsevier, New York

    Google Scholar 

  6. Sheldon RA, Kochi JK (1981) Metal-catalyzed oxidation of organic compounds. Academic Press, New York

    Google Scholar 

  7. Jacobsen EN (1993) In: Ojima I (ed) Catalytic asymmetric synthesis, VCH, Weinheim

  8. Katsuki T (1995) Coord Chem Rev 140:189

    Article  CAS  Google Scholar 

  9. Holm RH (1987) Chem Rev 87:1401

    Article  CAS  Google Scholar 

  10. Collman JP, Hegedus LS, Norton JR, Finke RG (eds) (1987) Principles and applications of organotransition metal chemistry. University Science Books, Mill Valley

    Google Scholar 

  11. Boghaei DM, Mohebi S (2002) J Mol Catal A 179:41

    Article  CAS  Google Scholar 

  12. Bagherzadeh M, Amini M (2009) Inorg Chem Commun 12:21

    Article  CAS  Google Scholar 

  13. Boghaei DM, Mohebi S (2002) Tetrahedron 58:5357

    Article  CAS  Google Scholar 

  14. Bagherzadeh M, Tahsini L, Latifi R, Ellern A, Woo LK (2008) Inorg Chim Acta 361:2019

    Article  CAS  Google Scholar 

  15. Bagherzadeh M, Latifi R, Tahsini L (2006) J Mol Catal A 260:163

    Article  CAS  Google Scholar 

  16. Bagherzadeh M, Tahsini L, Latifi R (2008) Catal Commun 9:1600

    Article  CAS  Google Scholar 

  17. Bagherzadeh M, Latifi R, Tahsini L, Amini M (2008) Catal Commun 10:196

    Article  CAS  Google Scholar 

  18. Wieghardt K (1989) Angew Chem Int Ed Engl 28:1153

    Article  Google Scholar 

  19. Kessissoglou DP (1999) Coord Chem Rev 185/186:837

    Google Scholar 

  20. Koek JH, Kohlen EWMJ, Russell SW, van der Wolf L, ter Steeg PF, Hellemons JC (1999) Inorg Chim Acta 295:189

    Article  CAS  Google Scholar 

  21. Bagherzadeh M (2003) Tetrahedron Lett 44:894322

    Article  Google Scholar 

  22. Limburg J, Vrettos JS, Liable-Sands LM, Rheingold AL, Crabtree RH, Brudvig GW (1999) Science 283:1524

    Article  CAS  Google Scholar 

  23. Das S, Incarvito CD, Crabtree RH, Brudvig GW (2006) Science 312:1941

    Article  CAS  Google Scholar 

  24. Chiswell B, McKenzie ED, Lindoy LF (1987) In: Wilkinson G, Gillard RD, McCleverty JA (eds) Comprehensive coordination chemistry, vol 4. Pergamon Press, Oxford

  25. Louloudi M, Nastopoulos V, Gourbatsis S, Perlepes SP, Hadjiliadis N (1999) Inorg Chem Commun 2:479

    Article  CAS  Google Scholar 

  26. Drummond J, Wood JS (1970) J Chem Soc A 226

  27. Andrew JE, Blake AB, Fraser LR (1975) J Chem Soc Dalton Trans 800

  28. Milinski N, Ribar B, Culum Z, Djuric S (1977) Acta Crystallogr B 33:1678

    Article  Google Scholar 

  29. Mikuriya M, Hatano Y, Asato E (1997) Bull Chem Soc Jpn 70:2495

    Article  CAS  Google Scholar 

  30. Hughes BB, Haltiwanger RC, Pierpont CG, Hampton M, Blackmer GL (1980) Inorg Chem 19:1801

    Article  CAS  Google Scholar 

  31. Reid HON, Kahwa IA, White AJP, Williams DJ (1998) Inorg Chem 37:3868

    Article  CAS  Google Scholar 

  32. Vaira MD, Mani F, Stoppioni P (1992) J Chem Soc Dalton Trans 1127

  33. Hagen KS (1992) Angew Chem Int Ed Engl 31:764

    Article  Google Scholar 

  34. Collins P, Diehl H (1960) Anal Chem Acta 2:125

    Article  Google Scholar 

  35. Diehl H, Buchanan EB, Smith GF (1960) Anal Chem 32:1117

    Article  CAS  Google Scholar 

  36. Embry WA, Ayres GH (1968) Anal Chem 40:1499

    Article  CAS  Google Scholar 

  37. Janmohamed MJ, Ayres GH (1972) Anal Chem 44:2263

    Article  CAS  Google Scholar 

  38. Majumder A, Choudhury CR, Mitra S, Marschner C, Baumgartner J (2005) Z Naturforsch 60b:99

  39. Zhang M, Fang R, Zhao Q (2008) J Chem Crystallogr 38:601

    Article  CAS  Google Scholar 

  40. Das A, Rosair GM, Fallah MS, Ribas J, Mitra S (2006) Inorg Chem 45:3301

    Article  CAS  Google Scholar 

  41. Rankin KN, Liu Q, Hendry J, Yee H, Noureldin NA, Lee DG (1998) Tetrahedron Lett 39:1095

    Article  CAS  Google Scholar 

  42. Ley SV, Madin A (1991) In: Trost BM, Flemming I (eds) Comprehensive organic synthesis, vol 7. Pergamon Press, Oxford, 251 pp

  43. Ley SV, Norman J, Griffith WP, Marsden SP (1994) Synthesis 639

  44. Stevens RV, Chapman KT, Waiter HN (1980) J Org Chem 45:2030

    Article  CAS  Google Scholar 

  45. Wozniak LA, Stec WJ (1999) Tetrahedron Lett 40:2637

    Article  CAS  Google Scholar 

  46. Wozniak LA, Koziolkiewicz M, Kobylanska A, Stec WJ (1998) Bioorg Med Chem Lett 8:2641

    Article  CAS  Google Scholar 

  47. Webb KS, Levy D (1995) Tetrahedron Lett 36:5117

    CAS  Google Scholar 

  48. Webb KS, Ruszkay SJ (1998) Tetrahedron 54:401

    Article  CAS  Google Scholar 

  49. Trost BM (1981) Tetrahedron Lett 22:1287

    Article  CAS  Google Scholar 

  50. Baumstark AL, Beeson M, Vasquez PC (1989) Tetrahedron Lett 30:5567

    Article  CAS  Google Scholar 

  51. Sheldrick GM (2001) SHELXTL version 6.12. Bruker AXS, Madison

  52. Nakamoto K (1986) Infrared and Raman spectra of inorganic and coordination compounds, 4th edn. Wiley-Interscience Publication, New York

  53. Campos Fernandez CS (2001) Ph.D thesis, Michigan state University

  54. Majumder A, Choudhury CR, Mitra S, Marschner C, Baumgartner J (2005) Z Naturforsch 60b:99

  55. Kim J, Han S (2002) Acta Crystallogr C 58:m521

    Article  Google Scholar 

  56. Janiak C (2000) J Chem Soc Dalton Trans 3885

  57. Mallat, Baiker A (2004) Chem Rev 104:3037

  58. Limburg J, Crabtree RH, Brudvig GW (2000) Inorg Chim Acta 297:301

    Article  CAS  Google Scholar 

  59. Limburg J, Brudvig GW, Crabtree RH (1997) J Am Chem Soc 119:2761

    Article  CAS  Google Scholar 

  60. Thorp HH, Brudvig GW (1991) New J Chem 15:479

    CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to the Research Council of Sharif University of Technology and National Elite Foundation for their financial support.

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Correspondence to Davar M. Boghaei.

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Najafpour, M.M., Amini, M., Bagherzadeh, M. et al. Synthesis, structural characterization and alcohol oxidation activity of a new mononuclear manganese(II) complex. Transition Met Chem 35, 297–303 (2010). https://doi.org/10.1007/s11243-010-9327-4

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