Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst

Journal of the American Chemical Society

Volumn 125, Issue 26, 2003, Pages 7786-7787

  Kamijo, Shin ^a   Jin, Tienan ^a   Huo, Zhibao ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; COPPER COMPLEX; PALLADIUM COMPLEX; TRIAZOLE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ELECTRON TRANSPORT; REACTION ANALYSIS; REACTION OPTIMIZATION;

ALKYNES; CATALYSIS; COPPER; CYCLIZATION; PALLADIUM; TRIAZOLES;

EID: 0038541849     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034191s     Document Type: Article

References (28)

1. Reviews on 1,2,3-triazoles, see: (a) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, p 305.
2. (b) Wamhoff, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 5, p 669.
3. (a) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
4. (b) Rostovtscv, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
5. (c) Katrizky, A. R.; Singh, S. K. J. Org. Chem. 2002, 67, 9077.
6. (d) Journet, M.; Cai, D.; Kowal, J. J.; Larsen, R. D. Tetrahedron Lett. 2001, 42, 9117.
7. (a) Wiley, R. H.; Hussung, K. F.; Moffat, J. J. Org. Chem. 1956, 21, 190.
8. (b) Kirmse, v. W.; Horner, L. Liebigs Ann. Chem. 1958, 614, 1.
9. (c) Pasquale, R. J. D.; Padgett, C. D.; Rosser, R. W. J. Org. Chem. 1975, 40, 810.
10. (d) Abu-Orabi, S. T.; Atfah, M. A.; Jibril, I.; Mari'i, F. M.; Ali, A. A. J. Heterocycl. Chem. 1989, 26, 1461.
11. (e) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 9707.
12. (a) Huisgen, R.; Knorr, R.; Möbius, L.; Szeimies, G. Chem. Ber. 1965, 98, 4014.
13. (b) Huisgen, R.; Blaschke, H. Chem. Ber. 1965, 98, 2985.
14. (c) Woerner, F. P.; Reimlinger, H. Chem. Ber. 1970, 103, 1908.
15. Many years ago, the reactions between simple alkynes and simple azides were reported, but the combinations of the substrates were mostly limited to aryl alkynes and aryl or benzyl azides. (a) Gold, v. H. Liebigs Ann. Chem. 1965, 688, 205-216. (b) Winter, W.; Mülle, E. Chem. Ber. 1974, 107, 715.
16. Many years ago, the reactions between simple alkynes and simple azides were reported, but the combinations of the substrates were mostly limited to aryl alkynes and aryl or benzyl azides. (a) Gold, v. H. Liebigs Ann. Chem. 1965, 688, 205-216. (b) Winter, W.; Mülle, E. Chem. Ber. 1974, 107, 715.
17. Kamijo, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 2002, 41, 3230.
18. See Supporting Information for detailed data.
19. (a) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 9453.
20. (b) Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 11940.
21. (c) Kamijo, S.; Jin, T.; Yamamoto, Y. J. Org. Chem. 2002, 67, 7413.
22. (a) Kinugasa, M.; Hashimoto, S. J. Chem. Soc., Chem. Commun. 1972, 466.
23. (b) Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999.
24. (c) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572.
25. Analogous complexes are reported, see: (a) Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 221. (b) Reference 3e. (c) Reference 8c.
26. Analogous complexes are reported, see: (a) Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 221. (b) Reference 3e. (c) Reference 8c.
27. Analogous complexes are reported, see: (a) Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 221. (b) Reference 3e. (c) Reference 8c.
28. Moltzen, E. K.; Pedersen, H.; Bøgesø, K. P.; Meier, E.; Frederiksen, K.; Sánchez, C.; Lembøl, H. L. J. Med. Chem. 1994, 37, 4085.