Skip to main content
Log in

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

  • Articles
  • SPECIAL TOPIC · Organic Photochemistry
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Lahm GP, Cordova D, Barry JD. Bioorg Med Chem, 2009, 17: 4127–4133

    Article  CAS  Google Scholar 

  2. Lamberth C. Heterocycles, 2007, 71: 1467–1502

    Article  CAS  Google Scholar 

  3. Gilchrist TL. Heterocyclic Chemistry. 3rd Ed, England: Addison-Wesley Longman, 1998

    Google Scholar 

  4. 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: 3595–3605

    Article  CAS  Google Scholar 

  5. Kost AN, Grandberg II. Adv Heterocycl Chem, 1966, 6: 347–429

    Article  CAS  Google Scholar 

  6. Ojwach SO, Darkwa J. Inorg Chim Acta, 2011, 363: 1947–1964

    Article  Google Scholar 

  7. Singer RA, Doré M, Sieser JE, Berliner, MA. Tetrhedron Lett, 2006, 47: 3727–3731

    Article  CAS  Google Scholar 

  8. Kowalcyk R, Skarzewski J. Tetrahedron, 2005, 61: 623–628

    Article  Google Scholar 

  9. Singer RA, Caron S, McDermott RE, Arpin P, Do NM. Synthesis, 2003: 1727–1731

    Google Scholar 

  10. Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem Rev, 2011, 111: 6984–7034

    Article  CAS  Google Scholar 

  11. Yet L. Pyrazoles. In: Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK, Eds. Comprehensive Heterocylic Chemistry III. Volume 4. Oxford: Pergamon Press, 2008. 1–141

    Chapter  Google Scholar 

  12. Elguero J. Pyrazoles. In: Katritzky AR, Rees CW, Scriven EFV, Eds. Comprehensive Heterocylic Chemistry II. Volume 3. Oxford: Pergamon Press, 1996. 1–75

    Chapter  Google Scholar 

  13. Elguero J. Pyrazoles and their benzo derivatives. In: Katritzky AR, Rees CW, Eds. Comprehensive Heterocyclic Chemistry. Volume 5. Oxford: Pergamon Press, 1984. 167–303

    Chapter  Google Scholar 

  14. Lévai A. ARKIVOC, 2005: 344–352

  15. Huang YR, Katzenellenbogen JA. Org Lett, 2000, 2: 2833–2836

    Article  CAS  Google Scholar 

  16. Powers DG, Casebier DS, Fokas D, Ryan WJ, Troth JR, Coffen DL. Tetrahedron, 1998, 54: 4085–4089

    Article  CAS  Google Scholar 

  17. Raiford LC, Peterson WJ. J Org Chem, 1936, 1: 544–551

    Article  Google Scholar 

  18. Auwers K, Heimke P. Liebigs Ann, 1927, 458: 186–220

    Article  Google Scholar 

  19. Bhatnagar I, George MV. Tetrahedron, 1968, 24: 1293–1298

    Article  CAS  Google Scholar 

  20. Dodwadmath RP, Wheeler TS. Proc Ind Acad Sci, 1935, 2: 438–451

    Google Scholar 

  21. Sabitha G, Reddy GS, Reddy CS, Fatima N, Yadav JS. Synthesis, 2003, 8: 1267–1271

    Google Scholar 

  22. Smith LI, Howard KL. J Am Chem Soc, 1943, 65: 159–164

    Article  CAS  Google Scholar 

  23. Gladstone WAF, Norman ROC. J Chem Soc Chem Commun, 1966: 1536–1540

    Google Scholar 

  24. Huisgen R, Seidel M, Wallbillich G, Knupfer H. Tetrahedron, 1962, 17: 3–29

    Article  CAS  Google Scholar 

  25. Zolfigol M, Azarifar D, Maleki B. Tetrahedron Lett, 2004, 45: 2181–2183

    Article  CAS  Google Scholar 

  26. Singh SP, Kumar D, Prakash O, Kapoor RP. Synth Commun, 1997, 27: 2683–2689

    Article  CAS  Google Scholar 

  27. Chai L, Zhao Y, Sheng Q, Liu ZQ. Tetrahedron Lett, 2006, 47: 9283–9285

    Article  CAS  Google Scholar 

  28. Su G, Wu WT, Wang JT, Wu LM. Chin Chem Lett, 2008, 19: 1013–1016

    Article  CAS  Google Scholar 

  29. Nakamichi N, Kawashita Y, Hayashi M. Org Lett, 2002, 4: 3955–3957

    Article  CAS  Google Scholar 

  30. Kawashita Y, Hayashi M. Molecules, 2009, 14: 3073–3093

    Article  CAS  Google Scholar 

  31. Nakamichi N, Kawashita Y, Hayashi M. Synthesis, 2004, 7: 1015–1020

    Google Scholar 

  32. Ananthnag GS, Adhikari A, Balakrishna MS. Catal Commun, 2014, 43: 240–243

    Article  CAS  Google Scholar 

  33. Schrader L. Tetrahedron Lett, 1971, 12: 2977–2980

    Article  Google Scholar 

  34. Evans NA, Leaver IH. Aust J Chem, 1974, 27: 1797–1803

    Article  CAS  Google Scholar 

  35. Evans NA, Rivett DE, Wilshire JFK. Aust J Chem, 1975, 27: 2267–2274

    Article  Google Scholar 

  36. Evans NA. Aust J Chem, 1975, 28: 433–437

    Article  CAS  Google Scholar 

  37. Traven VF, Ivanov IV. Russ Chem Bull Int Ed, 2008, 57: 1063–1069

    Article  CAS  Google Scholar 

  38. Schultz DM, Yoon TP. Science, 2014, 343: 1239176

  39. Prier CK, Rankic DA, MacMillan DWC. Chem Rev, 2013, 113: 5322–5363

    Article  CAS  Google Scholar 

  40. Tucker JW, Stephenson CRJ. J Org Chem, 2012, 77: 1617–1622

    Article  CAS  Google Scholar 

  41. Meng QY, Lei T, Zhao LM, Wu CJ, Zhong JJ, Gao XW, Tung CH, Wu LZ. Org Lett, 2014, 16: 5968–5971

    Article  CAS  Google Scholar 

  42. Zhong JJ, Meng QY, Wang GX, Liu Q, Chen B, Feng K, Tung, CH, Wu LZ. Chem Eur J, 2013, 19: 6443–6450

    Article  CAS  Google Scholar 

  43. Feng K, Zhang RY, Wu LZ, Tu B, Peng ML, Zhang LP, Zhao D, Tung CH. J Am Chem Soc, 2006, 128: 14685–14690

    Article  CAS  Google Scholar 

  44. Chan CW, Cheng LK, Che CM. Coord Chem Rev, 1994, 132, 87–97

    Article  CAS  Google Scholar 

  45. Roundhill DM, Gray HB, Che CM. Acc Chem Res, 1989, 22: 55–61

    Article  CAS  Google Scholar 

  46. Zhang D, Wu LZ, Zhou L, Han X, Yang QZ, Zhang LP, Tung CH. J Am Chem Soc, 2004, 126: 3440–3441

    Article  CAS  Google Scholar 

  47. Wang DH, Peng ML, Han Y, Chen B, Tung CH, Wu LZ. Inorg Chem, 2009, 48: 9995–9997

    Article  CAS  Google Scholar 

  48. Chen YZ, Wang DH, Chen B, Zhong JJ, Tung CH, Wu LZ. J Org Chem, 2012, 77: 6773–6777

    Article  CAS  Google Scholar 

  49. Narayana-Prabhu R, Schmehl RH. Inorg Chem, 2006, 45: 4319–4321

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Bin Chen or Li-Zhu Wu.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ye, P., Wang, DH., Chen, B. et al. Visible light catalyzed aromatization of 1,3,5-triaryl-2-pyrazolines by platinum(II) polypyridyl complex under oxidant-free condition. Sci. China Chem. 59, 175–179 (2016). https://doi.org/10.1007/s11426-016-5554-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-016-5554-7

Keywords

Navigation