Rhodium Complex-Catalyzed Reaction of Isonitriles with Carbonyl Compounds: Catalytic Synthesis of Pyrroles

Organic Letters

Volumn 3, Issue 3, 2001, Pages 421-424

  Takaya, Hikaru ^a   Kojima, Sachiko ^a   Murahashi, Shun Ichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001344043     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069296     Document Type: Article

References (38)

1. For a review on C-H activations by the α-heteroatom effect, see: Murahashi, S.-I.; Naota, T. Bull. Chem. Soc. Jpn. 1996, 69, 1805.
2. (a) Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348.
3. (b) Murahashi, S.-I.; Watanabe, T. J. Am. Chem. Soc. 1979, 101, 7429.
4. For reviews on C-H activations of nitriles, see: (a) Murahashi, S.-I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (b) Naota, T.; Murahashi, S.-I.; Takaya, H. Chem. Rev. 1998, 98, 2599.
5. For reviews on C-H activations of nitriles, see: (a) Murahashi, S.-I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225. (b) Naota, T.; Murahashi, S.-I.; Takaya, H. Chem. Rev. 1998, 98, 2599.
6. (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954.
7. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
8. (c) Takaya, H.; Naota, T.; Murahashi, S.-I. J. Am. Chem. Soc. 1998, 120, 4244.
9. (a) Noyori, R.; Ohta, M.; Hisiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117.
10. (b) Kitamura, M.; Hsiao, Y.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829.
11. Schöllkopf, U.; Gerhart, F.; Schröder, R. Anqew. Chem., Int. Ed. Engl. 1969, 8, 672.
12. Castejon, H. J.; Wiberg, K. B. J. Org. Chem. 1998, 63, 3937.
13. Bancroft, G. M.; Garrod, R. E. B.; Maddock, A. G.; Mays, M. J.; Prater, B. E. J. Am. Chem. Soc. 1972, 94, 647.
14. Kim, J. B.; Adler, A. D.; Longo, F. R.; Paine, J. B. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 1, pp 85-234.
15. Jones, R. A. In The Chemistry of Heterocyclic Compounds, Vol. 48, Pyrroles, Part 2; Taylor, E. C., Ed.; Wiley: New York, 1990.
16. (a) Jackson, A. H.; Smith, K. H. In The Total Synthesis of Natural Products: ApSimon, J., Ed.; Wiely: New York, 1973; Vol. 1, pp 143-278.
17. (b) Jones, R. A.; Bean, G. P. In The Chemistry of Pyrroles; Blomquist, A. T., Wasserman, H. H., Eds.; Academic Press: London, 1977.
18. (c) Patterson, J. M. Synthesis 1976, 281.
19. (a) Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1985, 1098.
20. (b) Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587.
21. (a) Murahashi, S.-I.; Shimamura, T.; Moritani, I. J. Chem. Soc., Chem. Commun. 1974, 931.
22. (b) Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981, 22, 4277.
23. (c) Chatani, N.; Hanafusa, T. J. Org. Chem. 1991, 56, 2166.
24. (d) Tsutsui, H.; Narasaka, K. Chem. Lett. 1999, 45.
25. For details see, the Supporting Infromation.
26. Paine, J. B., III.; Kirshner, W. B.; Moskowitz, D. W.; Dolphin, D. J. Org. Chem. 1976, 41, 3857.
27. For the synthesis of fluorinated pyrroles, see: (a) Kaesler, R. W.; Legoff, E. J. Org. Chem. 1982, 47, 4779. (b) Ogoshi, H.; Homma, M.; Toi, H.; Aoyama, Y. Tetrahedron Lett. 1983, 24, 929. (c) Burton, D. J.; Qiu, Z.-M. Tetrahedron Lett. 1994, 35, 4319. (d) Wang, J.; Scott, A. I. Tetrahedron 1994, 50, 6181. (e) Leroy, J.; Wakselman, C. Tetrahedron Lett. 1994, 35, 8605.
28. For the synthesis of fluorinated pyrroles, see: (a) Kaesler, R. W.; Legoff, E. J. Org. Chem. 1982, 47, 4779. (b) Ogoshi, H.; Homma, M.; Toi, H.; Aoyama, Y. Tetrahedron Lett. 1983, 24, 929. (c) Burton, D. J.; Qiu, Z.-M. Tetrahedron Lett. 1994, 35, 4319. (d) Wang, J.; Scott, A. I. Tetrahedron 1994, 50, 6181. (e) Leroy, J.; Wakselman, C. Tetrahedron Lett. 1994, 35, 8605.
29. For the synthesis of fluorinated pyrroles, see: (a) Kaesler, R. W.; Legoff, E. J. Org. Chem. 1982, 47, 4779. (b) Ogoshi, H.; Homma, M.; Toi, H.; Aoyama, Y. Tetrahedron Lett. 1983, 24, 929. (c) Burton, D. J.; Qiu, Z.-M. Tetrahedron Lett. 1994, 35, 4319. (d) Wang, J.; Scott, A. I. Tetrahedron 1994, 50, 6181. (e) Leroy, J.; Wakselman, C. Tetrahedron Lett. 1994, 35, 8605.
30. For the synthesis of fluorinated pyrroles, see: (a) Kaesler, R. W.; Legoff, E. J. Org. Chem. 1982, 47, 4779. (b) Ogoshi, H.; Homma, M.; Toi, H.; Aoyama, Y. Tetrahedron Lett. 1983, 24, 929. (c) Burton, D. J.; Qiu, Z.-M. Tetrahedron Lett. 1994, 35, 4319. (d) Wang, J.; Scott, A. I. Tetrahedron 1994, 50, 6181. (e) Leroy, J.; Wakselman, C. Tetrahedron Lett. 1994, 35, 8605.
31. For the synthesis of fluorinated pyrroles, see: (a) Kaesler, R. W.; Legoff, E. J. Org. Chem. 1982, 47, 4779. (b) Ogoshi, H.; Homma, M.; Toi, H.; Aoyama, Y. Tetrahedron Lett. 1983, 24, 929. (c) Burton, D. J.; Qiu, Z.-M. Tetrahedron Lett. 1994, 35, 4319. (d) Wang, J.; Scott, A. I. Tetrahedron 1994, 50, 6181. (e) Leroy, J.; Wakselman, C. Tetrahedron Lett. 1994, 35, 8605.
32. (a) Onda, H.; Toi, H.; Aoyama, Y.; Ogoshi, H. Tetrahedron Lett. 1985, 26, 4221.
33. (b) Tsuchiya, S.; Seno, M. Chem. Lett. 1989, 263.
34. (c) Woller, E. K.; DiMagno, S. G. J. Org. Chem. 1997, 61, 1588.
35. (d) Leroy, J.; Bondon, A.; Toupet, L.; Rolando, C. Chem. Eur. J. 1997, 3, 1890.
36. (e) Murahashi, S.-I.; Naota, T.; Komiya, N. Tetrahedron Lett. 1995, 36, 8059 and references therein.
37. Welch, J. T. Tetrahedron 1987, 43, 3123.
38. Zahalka, H. A.; Alper, H. Tetrahedron Lett. 1987, 28, 2215.