Science China Chemistry

, Volume 59, Issue 2, pp 175–179 | Cite as

Visible light catalyzed aromatization of 1,3,5-triaryl-2-pyrazolines by platinum(II) polypyridyl complex under oxidant-free condition

  • Pan Ye
  • Deng-Hui Wang
  • Bin Chen
  • Qing-Yuan Meng
  • Chen-Ho Tung
  • Li-Zhu Wu
Articles SPECIAL TOPIC · Organic Photochemistry


With visible light (λ=450 nm) irradiation of a catalytic amount of platinum(II) terpyridyl complex, 1,3,5-triaryl-2-pyrazolines can be smoothly converted to their corresponding pyrazoles and hydrogen in quantitative yields with no use of any oxidant at room temperature.


pyrazolines pyrazoles photoredox catalysis visible light platinum(II) terpyridyl complex 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

11426_2016_5554_MOESM1_ESM.pdf (2 mb)
Supplementary material, approximately 2024 KB.


  1. 1 a).
    Lahm GP, Cordova D, Barry JD. Bioorg Med Chem, 2009, 17: 4127–4133CrossRefGoogle Scholar
  2. b).
    Lamberth C. Heterocycles, 2007, 71: 1467–1502CrossRefGoogle Scholar
  3. c).
    Gilchrist TL. Heterocyclic Chemistry. 3rd Ed, England: Addison-Wesley Longman, 1998Google Scholar
  4. d).
    Ashton WT, Hutchins SM, Greenlee WJ, Doss GA, Chang RSL, Lotti VJ, Faust KA, Chen TB, Zingaro GJ, Kivlighn SD, Siegl PKS. J Med Chem, 1993, 36: 3595–3605CrossRefGoogle Scholar
  5. e).
    Kost AN, Grandberg II. Adv Heterocycl Chem, 1966, 6: 347–429CrossRefGoogle Scholar
  6. 2 |a).
    Ojwach SO, Darkwa J. Inorg Chim Acta, 2011, 363: 1947–1964CrossRefGoogle Scholar
  7. b).
    Singer RA, Doré M, Sieser JE, Berliner, MA. Tetrhedron Lett, 2006, 47: 3727–3731CrossRefGoogle Scholar
  8. c).
    Kowalcyk R, Skarzewski J. Tetrahedron, 2005, 61: 623–628CrossRefGoogle Scholar
  9. d).
    Singer RA, Caron S, McDermott RE, Arpin P, Do NM. Synthesis, 2003: 1727–1731Google Scholar
  10. 3 |a).
    Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem Rev, 2011, 111: 6984–7034CrossRefGoogle Scholar
  11. b).
    Yet L. Pyrazoles. In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK, Eds. Comprehensive Heterocylic Chemistry III. Volume 4. Oxford: Pergamon Press, 2008. 1–141CrossRefGoogle Scholar
  12. c).
    Elguero J. Pyrazoles. In: Katritzky AR, Rees CW, Scriven EFV, Eds. Comprehensive Heterocylic Chemistry II. Volume 3. Oxford: Pergamon Press, 1996. 1–75CrossRefGoogle Scholar
  13. d).
    Elguero J. Pyrazoles and their benzo derivatives. In: Katritzky AR, Rees CW, Eds. Comprehensive Heterocyclic Chemistry. Volume 5. Oxford: Pergamon Press, 1984. 167–303CrossRefGoogle Scholar
  14. 4 |a).
    Lévai A. ARKIVOC, 2005: 344–352Google Scholar
  15. b).
    Huang YR, Katzenellenbogen JA. Org Lett, 2000, 2: 2833–2836CrossRefGoogle Scholar
  16. c).
    Powers DG, Casebier DS, Fokas D, Ryan WJ, Troth JR, Coffen DL. Tetrahedron, 1998, 54: 4085–4089CrossRefGoogle Scholar
  17. d).
    Raiford LC, Peterson WJ. J Org Chem, 1936, 1: 544–551CrossRefGoogle Scholar
  18. 5.
    Auwers K, Heimke P. Liebigs Ann, 1927, 458: 186–220CrossRefGoogle Scholar
  19. 6.
    Bhatnagar I, George MV. Tetrahedron, 1968, 24: 1293–1298CrossRefGoogle Scholar
  20. 7.
    Dodwadmath RP, Wheeler TS. Proc Ind Acad Sci, 1935, 2: 438–451Google Scholar
  21. 8.
    Sabitha G, Reddy GS, Reddy CS, Fatima N, Yadav JS. Synthesis, 2003, 8: 1267–1271Google Scholar
  22. 9.
    Smith LI, Howard KL. J Am Chem Soc, 1943, 65: 159–164CrossRefGoogle Scholar
  23. 10.
    Gladstone WAF, Norman ROC. J Chem Soc Chem Commun, 1966: 1536–1540Google Scholar
  24. 11.
    Huisgen R, Seidel M, Wallbillich G, Knupfer H. Tetrahedron, 1962, 17: 3–29CrossRefGoogle Scholar
  25. 12.
    Zolfigol M, Azarifar D, Maleki B. Tetrahedron Lett, 2004, 45: 2181–2183CrossRefGoogle Scholar
  26. 13.
    Singh SP, Kumar D, Prakash O, Kapoor RP. Synth Commun, 1997, 27: 2683–2689CrossRefGoogle Scholar
  27. 14.
    Chai L, Zhao Y, Sheng Q, Liu ZQ. Tetrahedron Lett, 2006, 47: 9283–9285CrossRefGoogle Scholar
  28. 15.
    Su G, Wu WT, Wang JT, Wu LM. Chin Chem Lett, 2008, 19: 1013–1016CrossRefGoogle Scholar
  29. 16.
    Nakamichi N, Kawashita Y, Hayashi M. Org Lett, 2002, 4: 3955–3957CrossRefGoogle Scholar
  30. 17 |a).
    Kawashita Y, Hayashi M. Molecules, 2009, 14: 3073–3093CrossRefGoogle Scholar
  31. b).
    Nakamichi N, Kawashita Y, Hayashi M. Synthesis, 2004, 7: 1015–1020Google Scholar
  32. 18.
    Ananthnag GS, Adhikari A, Balakrishna MS. Catal Commun, 2014, 43: 240–243CrossRefGoogle Scholar
  33. 19.
    Schrader L. Tetrahedron Lett, 1971, 12: 2977–2980CrossRefGoogle Scholar
  34. 20 |a).
    Evans NA, Leaver IH. Aust J Chem, 1974, 27: 1797–1803CrossRefGoogle Scholar
  35. b).
    Evans NA, Rivett DE, Wilshire JFK. Aust J Chem, 1975, 27: 2267–2274CrossRefGoogle Scholar
  36. c).
    Evans NA. Aust J Chem, 1975, 28: 433–437CrossRefGoogle Scholar
  37. 21.
    Traven VF, Ivanov IV. Russ Chem Bull Int Ed, 2008, 57: 1063–1069CrossRefGoogle Scholar
  38. 22 |a).
    Schultz DM, Yoon TP. Science, 2014, 343: 1239176Google Scholar
  39. b).
    Prier CK, Rankic DA, MacMillan DWC. Chem Rev, 2013, 113: 5322–5363CrossRefGoogle Scholar
  40. b).
    Tucker JW, Stephenson CRJ. J Org Chem, 2012, 77: 1617–1622CrossRefGoogle Scholar
  41. 23 |a).
    Meng QY, Lei T, Zhao LM, Wu CJ, Zhong JJ, Gao XW, Tung CH, Wu LZ. Org Lett, 2014, 16: 5968–5971CrossRefGoogle Scholar
  42. b).
    Zhong JJ, Meng QY, Wang GX, Liu Q, Chen B, Feng K, Tung, CH, Wu LZ. Chem Eur J, 2013, 19: 6443–6450CrossRefGoogle Scholar
  43. c).
    Feng K, Zhang RY, Wu LZ, Tu B, Peng ML, Zhang LP, Zhao D, Tung CH. J Am Chem Soc, 2006, 128: 14685–14690CrossRefGoogle Scholar
  44. d).
    Chan CW, Cheng LK, Che CM. Coord Chem Rev, 1994, 132, 87–97CrossRefGoogle Scholar
  45. e).
    Roundhill DM, Gray HB, Che CM. Acc Chem Res, 1989, 22: 55–61CrossRefGoogle Scholar
  46. 24.
    Zhang D, Wu LZ, Zhou L, Han X, Yang QZ, Zhang LP, Tung CH. J Am Chem Soc, 2004, 126: 3440–3441CrossRefGoogle Scholar
  47. 25.
    Wang DH, Peng ML, Han Y, Chen B, Tung CH, Wu LZ. Inorg Chem, 2009, 48: 9995–9997CrossRefGoogle Scholar
  48. 26.
    Chen YZ, Wang DH, Chen B, Zhong JJ, Tung CH, Wu LZ. J Org Chem, 2012, 77: 6773–6777CrossRefGoogle Scholar
  49. 27.
    Narayana-Prabhu R, Schmehl RH. Inorg Chem, 2006, 45: 4319–4321CrossRefGoogle Scholar

Copyright information

© Science China Press and Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringShandong UniversityJinanChina
  2. 2.Key Laboratory of Photochemical Conversion and Optoelectronic Materials; Technical Institute of Physics and ChemistryChinese Academy of SciencesBeijingChina

Personalised recommendations