A novel three-component coupling reaction of arynes, isocyanides, and cyanoformates: A straightforward access to cyano-substituted iminoisobenzofurans

Heterocycles

Volumn 86, Issue 2, 2012, Pages 933-940

  Li, Jing ^a   Noyori, Shintaro ^a   Iwasaki, Masayuki ^a   Nakajima, Kiyohiko ^b   Nishihara, Yasushi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84880591620     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-12-S(N)77     Document Type: Article

References (44)

1. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York, 1967;
2. H. Hart, The Chemistry of Triple-Bonded Functional Groups, Supplement C2 (ed. by S. Pata, Wiley, Chichester, 1994, chap. 18;
3. H. Pellissier and M. Santelli, Tetrahedron, 2003, 59, 701;
4. H. H. Wenk, M. Winkler, and W. Sander, Angew. Chem. Int. Ed., 2003, 42, 502;
5. D. Peña, D. Pérez, and E. Guitián, Angew. Chem. Int. Ed., 2006, 45, 3579;
6. S. S. Bhojgude and A. T. Biju, Angew. Chem. Int. Ed., 2012, 51, 1520;
7. F. Sha, L. Wu, and X. Huang, J. Org. Chem., 2012, 77, 3754.
8. Y. Nishihara, Y. Inoue, M. Itazaki, and K. Takagi, Org. Lett., 2005, 7, 2639;
9. Y. Nishihara, Y. Inoue, S. Izawa, M. Miyasaka, K. Tanemura, K. Nakajima, and K. Takagi, Tetrahedron, 2006, 62, 9872;
10. Y. Nishihara, M. Miyasaka, Y. Inoue, T. Yamaguchi, M. Kojima, and K. Takagi, Organometallics, 2007, 26, 4054.
11. Y. Himeshima, T. Sonoda, and H. Kobayashi, Chem. Lett., 1983, 1211.
12. H. Yoshida, H. Fukushima, J. Ohshita, and A. Kunai, Angew. Chem. Int. Ed., 2004, 43, 3935;
13. H. Yoshida, H. Fukushima, T. Morishita, J. Ohshita, and A. Kunai, Tetrahedron, 2007, 63, 4793;
14. H. Yoshida and K. Takaki, Heterocycles, 2012, 85, 1333.
15. K. M. Allan, C. D. Gilmore, and B. M. Stoltz, Angew. Chem. Int. Ed., 2011, 50, 4488.
16. Y. Ito, H. Kato, and T. Saegusa, J. Org. Chem., 1982, 47, 741;
17. A. I. Meyers, M. A. Hanagan, L. M. Trefonas, and R. J. Baker, Tetrahedron, 1983, 39, 1991;
18. V. Nair and A. U. Vinod, Chem. Commun., 2000, 1019;
19. A. Fayol and J. Zhu, Angew. Chem. Int. Ed., 2002, 41, 3633;
20. N. Chatani, M. Oshita, M. Tobisu, Y. Ishii, and S. Murai, J. Am. Chem. Soc., 2003, 125, 7812;
21. A. Fayol and J. Zhu, Org. Lett., 2004, 6, 115;
22. A. V. Lygin and A. de Meijere, J. Org. Chem., 2009, 74, 4554;
23. K. Kobayashi, S. Fujita, D. Nakai, S. Fukumoto, S. Fukamachi, and H. Konishi, Helv. Chim. Acta, 2010, 93, 1274;
24. K. Kobayashi, Y. Shirai, S. Fukamachi, and H. Konishi, Synthesis, 2010, 666;
25. Z.-Y. Yan, C.-M. Tan, X. Wang, F. Li, G.-L. Gao, X.-M. Chen, W.-S. Wu, and J.-J. Wang, Synlett, 2011, 1863;
26. D. Chen, G.-Y. Song, A. Jia, and X.-W. Li, J. Org. Chem., 2011, 76, 8488;
27. K. Kobayashi, K. Matsumoto, and H. Konishi, Heterocycles, 2011, 83, 99.
28. G. Carturan, M. Biasiolo, S. Daniele, G. A. Mazzocchin, and P. Ugo, Inorg. Chim. Acta, 1986, 119, 19.
29. H.-B. Qiu, Y. Inoue, and S.-N. Che, Angew. Chem. Int. Ed., 2009, 48, 3069.
30. T. Hirakawa, K. Ikeda, H. Ogasa, M. Kawatsura, and T. Itoh, Synlett, 2010, 2887.
31. Y. Du, T. K. Hyster, and T. Rovis, Chem. Commun., 2011, 47, 12074.
32. S. Oi, K. Kashiwagi, E. Terada, K. Ohuchi, and Y. lnoue, Tetrahedron Lett., 1996, 37, 6351.
33. S. V. Kessar, Comprehensive Organic Synthesis, Vol. 4 (ed. by B. M. Trost and I. Flemin, Pergamon, Oxford, 1991, pp. 483-515;
34. E. R. Biehl and S. P. Khanapure, Acc. Chem. Res., 1989, 22, 275.
35. E. Yoshikawa and Y. Yamamoto, Angew. Chem. Int. Ed., 2000, 39, 173;
36. N. Chatani, A. Kamitani, M. Oshita, Y. Fukumoto, and S. Murai, J. Am. Chem. Soc., 2001, 123, 12686;
37. H. Yoshida, H. Fukushima, J. Ohshita, and A. Kunai, Tetrahedron Lett., 2004, 45, 8659;
38. T. T. Jayanth, M. Jeganmohan, and C.-H. Cheng, Org. Lett., 2005, 7, 2921;
39. J. L. Henderson, A. S. Edwards, and M. F. Greaney, J. Am. Chem. Soc., 2006, 128, 7426;
40. M. Jeganmohan and C.-H. Cheng, Chem. Commun., 2006, 2454;
41. H. Yoshida, H. Fukushima, J. Ohshita, and A. Kunai, J. Am. Chem. Soc., 2006, 128, 11040;
42. I. Larrosa, M. I. Da Silva, P. M. Gómez, P. Hannen, E. Ko, S. R. Lenger, S. R. Linke, A. J. P. White, D. Wilton, and A. G. M. Barrett, J. Am. Chem. Soc., 2006, 128, 14042;
43. F. Sha and X. Huang, Angew. Chem. Int. Ed., 2009, 48, 3458;
44. E. Yoshioka, S. Kohtani, and H. Miyabe, Angew. Chem. Int. Ed., 2011, 50, 6638.