Palladium-catalyzed alkenylation of 1,2,3-trizoles with terminal conjugated alkenes by direct C - H bond functionalization

European Journal of Organic Chemistry

Volumn , Issue 7, 2010, Pages 1227-1230

  Jiang, Huanfeng ^a   Feng, Zhenning ^a   Wang, Azhong ^a   Liu, Xiaohang ^a   Chen, Zhengwang ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Alkenes; Alkenylation; C H functionalization; Nitrogen heterocycles; Palladium

Indexed keywords

EID: 77149145205     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901282     Document Type: Article

References (31)

1. Reviews on 1,2,3-triazoles: a) H. Dehne in Methoden der Organischen Chemie (Houben-Weyl) (Ed.: E. Schumann), Thieme, Stuttgart, 1994, vol. 8, p. 305;
2. b) H. Wamhoff in Comprehensive Heterocyclic Chemistry (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, vol. 5, p. 669;
3. c) P. Desai, K. Schildknegt, K. A. Agrios, C. Mossman, G. Milligan, J. Aube, J. Am. Chem. Soc. 2000, 122, 7226-7232.
4. a) C. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064;
5. b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
6. S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org. Lett. 2007, 9, 2333-2336.
7. a) L. Ackermann, H. K. Potukuchi, D. Landsberg, R. Vicente, Org. Lett. 2008, 10, 3081-3084;
8. b) L. Ackermann, R. Vicente, R. Born, Adv. Synth. Catal. 2008, 350, 741-748;
9. c) L. Ackermann, R. Vicente, Org. Lett. 2009, 11, 4922-4925;
10. d) L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. Int. Ed. 2009, 48, 201-204.
11. J. Deng, Y. M. Wu, Q. Y. Chen, Synthesis 2005, 16, 2730-2738.
12. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318-5365.
13. a) I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 8, 1119-1122;
14. b) Y. Fujiwara, I. Moritani, S. Danno, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166-7169;
15. c) Y. Fujiwara, O. Maruyama, M. Yoshidomi, H. Taniguchi, J. Org. Chem. 1981, 46, 851-855;
16. d) C. G. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633-639.
17. a) Y. Fujiwara, R. Asano, I. Moritani, S. Teranishi, J. Org. Chem. 1976, 41, 1681-1683;
18. b) C. G. Jia,W. J. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097-2100;
19. c) A. Maehara, T. Satoh, M. Miura, Tetrahedron 2008, 64, 5982-5986;
20. d) J. L. Zhao, L. H. Huang, K. Cheng, Y. H. Zhang, Tetrahedron Lett. 2009, 50, 2758-2761.
21. For intermolecular direct alkenylation reactions of indoles and pyrroles, see: a) N. P. Grimster, C. Gauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. Int. Ed. 2005, 44, 3125-3129;
22. b) E. M. Beck, N. P. Grimster, R. H. Hatley, M. J. Gaunt, J. Am. Chem. Soc. 2006, 128, 2528-2529;
23. c) E. M. Beck, R. Hatley, M. J. Gaunt, Angew. Chem. Int. Ed. 2008, 47, 3004-3007.
24. T. Itahara, K. Kawasaki, F. Ouseto, Bull. Chem. Soc. Jpn. 1984, 57, 3488-3493.
25. For intramolecular direct alkenylation reactions examples, see: a) H. Zhang, E. M. Ferreira, B. M. Stoltz, Angew. Chem. Int. Ed. 2004, 43, 6144-6148;
26. b) H. Iida, Y. Yuasa, C. Kibayashi, J. Org. Chem. 1980, 45, 2938-2942;
27. c) H. J. Knölker, N. O'Sullivan, Tetrahedron 1994, 50, 10893-10908.
28. a) T. Yokota, M. Tani, S. Sakaguchi, Y. Ishii, J. Am. Chem. Soc. 2003, 125, 1476-1477;
29. b) Y. Hatamoto, S. Sakaguchi, Y. Ishii, Org. Lett. 2004, 6, 4623-4625;
30. c) T. Yamada, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2005, 70, 5471-5474.
31. The structure of 3aj was determined by NOESY. See Supporting Information for details.