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.
Similar content being viewed by others
References
Lahm GP, Cordova D, Barry JD. Bioorg Med Chem, 2009, 17: 4127–4133
Lamberth C. Heterocycles, 2007, 71: 1467–1502
Gilchrist TL. Heterocyclic Chemistry. 3rd Ed, England: Addison-Wesley Longman, 1998
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
Kost AN, Grandberg II. Adv Heterocycl Chem, 1966, 6: 347–429
Ojwach SO, Darkwa J. Inorg Chim Acta, 2011, 363: 1947–1964
Singer RA, Doré M, Sieser JE, Berliner, MA. Tetrhedron Lett, 2006, 47: 3727–3731
Kowalcyk R, Skarzewski J. Tetrahedron, 2005, 61: 623–628
Singer RA, Caron S, McDermott RE, Arpin P, Do NM. Synthesis, 2003: 1727–1731
Fustero S, Sánchez-Roselló M, Barrio P, Simón-Fuentes A. Chem Rev, 2011, 111: 6984–7034
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
Elguero J. Pyrazoles. In: Katritzky AR, Rees CW, Scriven EFV, Eds. Comprehensive Heterocylic Chemistry II. Volume 3. Oxford: Pergamon Press, 1996. 1–75
Elguero J. Pyrazoles and their benzo derivatives. In: Katritzky AR, Rees CW, Eds. Comprehensive Heterocyclic Chemistry. Volume 5. Oxford: Pergamon Press, 1984. 167–303
Lévai A. ARKIVOC, 2005: 344–352
Huang YR, Katzenellenbogen JA. Org Lett, 2000, 2: 2833–2836
Powers DG, Casebier DS, Fokas D, Ryan WJ, Troth JR, Coffen DL. Tetrahedron, 1998, 54: 4085–4089
Raiford LC, Peterson WJ. J Org Chem, 1936, 1: 544–551
Auwers K, Heimke P. Liebigs Ann, 1927, 458: 186–220
Bhatnagar I, George MV. Tetrahedron, 1968, 24: 1293–1298
Dodwadmath RP, Wheeler TS. Proc Ind Acad Sci, 1935, 2: 438–451
Sabitha G, Reddy GS, Reddy CS, Fatima N, Yadav JS. Synthesis, 2003, 8: 1267–1271
Smith LI, Howard KL. J Am Chem Soc, 1943, 65: 159–164
Gladstone WAF, Norman ROC. J Chem Soc Chem Commun, 1966: 1536–1540
Huisgen R, Seidel M, Wallbillich G, Knupfer H. Tetrahedron, 1962, 17: 3–29
Zolfigol M, Azarifar D, Maleki B. Tetrahedron Lett, 2004, 45: 2181–2183
Singh SP, Kumar D, Prakash O, Kapoor RP. Synth Commun, 1997, 27: 2683–2689
Chai L, Zhao Y, Sheng Q, Liu ZQ. Tetrahedron Lett, 2006, 47: 9283–9285
Su G, Wu WT, Wang JT, Wu LM. Chin Chem Lett, 2008, 19: 1013–1016
Nakamichi N, Kawashita Y, Hayashi M. Org Lett, 2002, 4: 3955–3957
Kawashita Y, Hayashi M. Molecules, 2009, 14: 3073–3093
Nakamichi N, Kawashita Y, Hayashi M. Synthesis, 2004, 7: 1015–1020
Ananthnag GS, Adhikari A, Balakrishna MS. Catal Commun, 2014, 43: 240–243
Schrader L. Tetrahedron Lett, 1971, 12: 2977–2980
Evans NA, Leaver IH. Aust J Chem, 1974, 27: 1797–1803
Evans NA, Rivett DE, Wilshire JFK. Aust J Chem, 1975, 27: 2267–2274
Evans NA. Aust J Chem, 1975, 28: 433–437
Traven VF, Ivanov IV. Russ Chem Bull Int Ed, 2008, 57: 1063–1069
Schultz DM, Yoon TP. Science, 2014, 343: 1239176
Prier CK, Rankic DA, MacMillan DWC. Chem Rev, 2013, 113: 5322–5363
Tucker JW, Stephenson CRJ. J Org Chem, 2012, 77: 1617–1622
Meng QY, Lei T, Zhao LM, Wu CJ, Zhong JJ, Gao XW, Tung CH, Wu LZ. Org Lett, 2014, 16: 5968–5971
Zhong JJ, Meng QY, Wang GX, Liu Q, Chen B, Feng K, Tung, CH, Wu LZ. Chem Eur J, 2013, 19: 6443–6450
Feng K, Zhang RY, Wu LZ, Tu B, Peng ML, Zhang LP, Zhao D, Tung CH. J Am Chem Soc, 2006, 128: 14685–14690
Chan CW, Cheng LK, Che CM. Coord Chem Rev, 1994, 132, 87–97
Roundhill DM, Gray HB, Che CM. Acc Chem Res, 1989, 22: 55–61
Zhang D, Wu LZ, Zhou L, Han X, Yang QZ, Zhang LP, Tung CH. J Am Chem Soc, 2004, 126: 3440–3441
Wang DH, Peng ML, Han Y, Chen B, Tung CH, Wu LZ. Inorg Chem, 2009, 48: 9995–9997
Chen YZ, Wang DH, Chen B, Zhong JJ, Tung CH, Wu LZ. J Org Chem, 2012, 77: 6773–6777
Narayana-Prabhu R, Schmehl RH. Inorg Chem, 2006, 45: 4319–4321
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Rights and permissions
About this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-016-5554-7