RuH 2(CO)(PPh 3) 3 catalyzed selective formation of 1,4-disubstituted triazoles from cycloaddition of alkynes and organic azides

Journal of Organic Chemistry

Volumn 77, Issue 13, 2012, Pages 5844-5849

  Liu, Pei Nian ^a   Siyang, Hai Xiao ^a   Zhang, Li ^b   Tse, Sunny Kai San ^b   Jia, Guochen ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,2 ,3-TRIAZOLES; CYCLOADDITION REACTION; ORGANIC AZIDES; RUTHENIUM HYDRIDE COMPLEX; SELECTIVE FORMATION; TERMINAL ALKYNE;

CYCLOADDITION; NITROGEN COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS;

ACETYLENE;

1 (4 IODOBENZYL) 4 PHENYL 1H 1,2,3 TRIAZOLE; 1 (4 METHOXYPHENETHYL) 4 PHENYL 1H 1,2,3 TRIAZOLE; 1 (4 METHYLBENZYL) 4 PHENYL 1H 1,2,3TRIAZOLE; 1 (N DODECYL) 4 (PHENYL) 1H 1.2.E 1,2,3 TRIAZOLE; 1 [4 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)PHENYL)ESTRADIOL; 1 [4 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)PHENYL]ETHANONE; 1 BENZYL 4 (4 FLUOROPHENYL) 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 4 TOLYL 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 CYCLOHEXYL 1H 1,2,3 TRIAZOLE; 1 BENZYL 4 FERROCENYL 1,2,3 TRIAZOLE; 1 BENZYL 4 PHENYL 1H 1,2,3 TRIAZOLE; 1 CYCLOHEXYL 4 PHENYL 1H 1,2,3 TRIAZOLE; 4 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)BENZENAMINE; 4 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)BUTAN 1 OL; 4 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)BUTANENITRILE; 4BETA (4 PHENYL 1,2,3 TRIAZOLE) 1 PODOPHYLLOTOXIN; ALKYNE; AZIDE; ETHYL 4 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)BENZOATE; RUTHENIUM COMPLEX; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ORGANOMETALLIC COMPOUND; RUTHENIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; SUBSTITUTION REACTION; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RUTHENIUM; TRIAZOLES;

EID: 84863611717     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3008572     Document Type: Article

References (49)

1. Lwowski, W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 559.
2. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2002.
3. Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565
4. Reactions involving activated alkynes or strained alkynes can be accomplished under relatively mild conditions. See: Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272
5. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210
6. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057
7. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596
8. Theme issue on Click chemistry: Chem. Soc. Rev. 2010, (4), 39. For additional reviews, see
9. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952
10. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249 and the references therein
11. Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278
12. Lutz, J.-F.; Zarafshani, Z. Adv. Drug Delivery Rev. 2008, 60, 958
13. Fokin, V. V. ACS Chem. Biol. 2007, 2, 775
14. Johnson, J. A.; Koberstein, J. T.; Finn, M. G.; Turro, N. J. Macromol. Rapid Commun. 2008, 29, 1052
15. Wu, P.; Fokin, V. V. Aldrichimica Acta 2007, 40, 7
16. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302
17. Zn/C catalyzed reactions: Meng, X.; Xu, X.; Gao, T.; Chen, B. Eur. J. Org. Chem. 2010, 5409
18. 4OH catalyzed reactions: Kwok, S. W.; Fosing, J. R.; Fraser, R.; Rodionov, V. O.; Fokin, V. V. Org. Lett. 2010, 12, 4217
19. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998
20. Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923
21. Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337
22. Oppilliart, S.; Mousseau, G.; Zhang, L.; Jia, G.; Thuéry, P.; Rousseau, B.; Cintrat, J. C. Tetrahedron 2007, 63, 8094
23. Hou, D. R.; Kuan, T. C.; Li, Y. K.; Lee, R.; Huang, K. W. Tetrahedron Lett. 2010, 66, 9415
24. Yap, A. H.; Weinreb, S. M. Tetrahedron Lett. 2006, 47, 3035
25. Majireck, M. M.; Weinreb, S. M. J. Org. Chem. 2006, 71, 8680
26. Johansson, J. R.; Lincoln, P.; Norden, B.; Kann, N. J. Org. Chem. 2011, 76, 2355
27. Empting, M.; Avrutina, O.; Meusinger, R.; Fabritz, S.; Reinwarth, M.; Biesalski, M.; Voigt, S.; Buntkowsky, G.; Kolmar, H. Angew. Chem., Int. Ed. 2011, 50, 5207
28. Chardon, E.; Puleo, G. L.; Dahm, G.; Guihard, G.; Bellemin,-Laponnaz, S. Chem. Commun. 2011, 47, 5864
29. Isidro,-Llobet, A.; Murillo, T.; Bello, P.; Cilibrizzi, A.; Hodgkinson, J. T.; Galloway, W. R. J. D.; Bender, A.; Welch, M.; Spring, D. R. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 6793
30. Poecke, S. V.; Negri, A.; Gago, F.; Daele, I. V.; Solaroli, N.; Karlsson, A.; Balzarini, J.; Calenbergh, S. V. J. Med. Chem. 2010, 53, 2902
31. Krause, M. R.; Goddard, R.; Kubik, S. Chem. Commun. 2010, 46, 5307
32. Horne, W. S.; Olsen, C. A.; Beierle, J. M.; Montero, A.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2009, 48, 4718
33. Chemama, M.; Fonvielle, M.; Arthur, M.; Valery, J. M.; Etheve-Quelquejeu, M. Chem.-Eur. J. 2009, 15, 1929
34. Kelly, A. W.; Wei, J.; Kesavan, K.; Marie, J.-C.; Windmon, N.; Young, D. W.; Maucaurelle, L. A. Org. Lett. 2009, 11, 2257
35. Yousefzadi, M.; Sharifi, M.; Behmanesh, M.; Moyano, E.; Bonfill, M.; Cusido, R. M.; Palazon, J. Eng. Life Sci. 2010, 10, 281
36. Garcia, E. S.; Azambuja, P. Toxicon 2004, 44, 431
37. Asano, K.; Matsubara, S. Org. Lett. 2010, 12, 4988
38. Zhou, X.-M.; Wang, Z.-Q.; Chang, J.-Y.; Chen, H.-X.; Cheng, Y.-C.; Lee, K.-H. J. Med. Chem. 1991, 34, 3346
39. Dash, B. P.; Satapathy, R.; Gaillard, E. R.; Norton, K. M.; Maguire, J. A.; Chug, N.; Hosmane, N. S. Inorg. Chem. 2011, 50, 5485
40. López-Pérez, J. L.; Olmo, E.; Pascual-Teresa, B.; Abad, A.; Feliciano, A. S. Bioorg. Med. Chem. Lett. 2004, 14, 1283
41. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F.; Wonchoba, E. R.; Parshall, G. W. Inorg. Synth. 1974, 15, 45
42. Lórincz, K.; Kele, P.; Novák, Z. Synthesis 2009, 3527
43. Wang, D.; Li, N.; Zhao, M.; Shi, W.; Ma, C.; Chen, B. Green Chem. 2010, 12, 2120
44. Zhou, Y.; Lecourt, T.; Micouin, L. Angew. Chem., Int. Ed. 2010, 49, 2607
45. Chassaing, S.; Sido, A. S. S.; Alix, A.; Kumarraja, M.; Pale, P.; Sommer, J. Chem.-Eur. J. 2008, 14, 6713
46. González, J.; Pérez, V. M.; Jiménez, D. O.; Lopez-Valdez, G.; Corona, D.; Cuevas-Yañez, E. Tetrahedron Lett. 2011, 3514
47. Gonda, Z.; Novák, Z. Dalton Trans. 2010, 39, 726
48. Alonso, F.; Moglie, Y.; Radivoy, G.; Yus, M. Eur. J. Org. Chem. 2010, 1875
49. Shi, J. F.; Wang, Y. G. Chin. J. Org. Chem. 2003, 11, 1244