Doyle-kirmse reaction using triazoles leading to one-pot multifunctionalization of terminal alkynes

Chemistry Letters

Volumn 42, Issue 10, 2013, Pages 1308-1310

  Miura, Tomoya ^a   Tanaka, Takamasa ^a   Yada, Akira ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84885339265     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.130521     Document Type: Review

References (30)

1. a) E. J. Yoo, M. Ahlquist, S. H. Kim, I. Bae, V. V. Fokin, K. B. Sharpless, S. Chang, Angew. Chem., Int. Ed. 2007, 46, 1730.
2. J. Raushel, V. V. Fokin, Org. Lett. 2010, 12, 4952.
3. Y. Liu, X. Wang, J. Xu, Q. Zhang, Y. Zhao, Y. Hu, Tetrahedron 2011, 67, 6294.
4. For reviews see: a) B. Chattopadhyay, V. Gevorgyan, Angew. Chem., Int. Ed. 2012, 51, 862.
5. A. V. Gulevich, V. Gevorgyan, Angew. Chem., Int. Ed. 2013, 52, 1371.
6. For rhodium (II)-catalyzed reactions, see: a) T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972.
7. S. Chuprakov, S. W. Kwok, L. Zhang, L. Lercher, V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034.
8. N. Grimster, L. Zhang, V. V. Fokin, J. Am. Chem. Soc. 2010, 132, 2510.
9. B. Chattopadhyay, V. Gevorgyan, Org. Lett. 2011, 13, 3746.
10. S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc. 2011, 133, 10352.
11. T. Miura, T. Biyajima, T. Fujii, M. Murakami, J. Am. Chem. Soc. 2012, 134, 194.
12. N. Selander, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 2477.
13. N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi, V. V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670.
14. T. Miura, Y. Funakoshi, M. Morimoto, T. Biyajima, M. Murakami, J. Am. Chem. Soc. 2012, 134, 17440.
15. N. Selander, B. T. Worrell, V. V. Fokin, Angew. Chem., Int. Ed. 2012, 51, 13054.
16. M. Zibinsky, V. V. Fokin, Angew. Chem., Int. Ed. 2013, 52, 1507.
17. T. Miura, T. Tanaka, T. Biyajima, A. Yada, M. Murakami, Angew. Chem., Int. Ed. 2013, 52, 3883.
18. S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652.
19. E. E. Schultz, R. Sarpong, J. Am. Chem. Soc. 2013, 135, 4696.
20. B. T. Parr, S. A. Green, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 4716.
21. J. E. Spangler, H. M. L. Davies, J. Am. Chem. Soc. 2013, 135, 6802.
22. For a nickel (0)-catalyzed reaction, see: T. Miura, M. Yamauchi, M. Murakami, Chem. Commun. 2009, 1470.
23. For a silver (I)-catalyzed reaction, see: R. Liu, M. Zhang, G. Winston-McPherson, W. Tang, Chem. Commun. 2013, 49, 4376.
24. For a review on a Doyle-Kirmse reaction, see: a) Y. Zhang, J. Wang, Coord. Chem. Rev. 2010, 254, 941.
25. For recent examples, see: b) D. S. Carter, D. L. Van Vranken, Org. Lett. 2000, 2, 1303.
26. Y. Kato, K. Miki, F. Nishino, K. Ohe, S. Uemura, Org. Lett. 2003, 5, 2619.
27. P. W. Davies, S. J.-C. Albrecht, G. Assanelli, Org. Biomol. Chem. 2009, 7, 1276.
28. Y. Li, Z. Huang, X. Wu, P.-F. Xu, J. Jin, Y. Zhang, J. Wang, Tetrahedron 2012, 68, 5234.
29. M. A. McKinney, P. P. Patel, J. Org. Chem. 1973, 38, 4059.
30. Supporting Information is available electronically on the CSJ-Journal Website, http://www.csj.jp/journals/chem-lett/index.html.