Palladium-Catalyzed Synthesis of 2-Substituted Indoles

Journal of Organic Chemistry

Volumn 54, Issue 25, 1989, Pages 5856-5866

  Rudisill, Duane E ^a   Stille, J K ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0024801018     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00286a014     Document Type: Article

References (22)

1. Trost, B. M.; Keinan, E. J. Org. Chem. 1980, 45, 2741. (b) Murahashi, S.; Shimamura, T.; Moritani, I. J. Chem. Soc., Chem. Commun. 1974, 931. (c) Utimoto, K.; Miwa, H.; Nazaki, H. Tetrahedron Lett. 1981, 22 4277.
2. Mizutani, M.; Sanemitsu, Y.; Tamaru, Y.; Yoshida, Z. Tetrahedron Lett. 1985, 26,1237. (b) Mitzutani, M.; Sanemitsu, Y. Tetrahedron 1986, 42, 305.
3. Kasahara, A.; Izumi, T.; Murakami, S.; Yanai, H.; Takatori, M. Bull. Chem. Soc. Jpn. 1986,59,927. (b) Yokoyama, Y.; Ito, S.; Takahashi, Y.; Murakami, Y. Tetrahedron Lett. 1985, 26, 6457. (c) Murakami, Y.; Yokoyama, A.; Aoki, T. Heterocycles 1984, 22,1493. (d) Tischler, A. N.; Lanza, T. J. Tetrahedron Lett. 1986,27,1653. (e) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 31. (f) Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984,106, 5759. (g) Harrington, P. J.; Hegedus, L. S.; McDaniel, K. F. J. Am. Chem. Soc. 1987,109, 4335. (h) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
4. For a recent review on organometallic methods for indole synthesis, see: (a) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988,27,1113. (b) Sakamoto, T.; Konda, Y.; Yamanaka, H. Heterocycles 1988, 27, 2225.
5. McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987. 52. 422.
6. Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170.
7. Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H. Tetrahedron Lett. 1985, 26, 5963.
8. Iritani, K.; Matsubara, S.; Utimoto, K. Tetrahedron Lett. 1988, 29,1799. (b) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305. (c) Arcadi, A.; Cacchi, S.; Marinelli. F. Tetrahedron Lett. 1989. 30. 2581.
9. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Stille. J. K. Pure Appl. Chem. 1985. 57, 1771.
10. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987,109, 5478.
11. Doyle, M. P.; Sigfried, B.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2426.
12. Johnson, J. R.; Sandborn, L. T. Organic Syntheses; Wiley: New York, 1951; Collect. Vol. I.,p 111.
13. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4981.
14. Byers, P. K.; Canty, A. J.; Skelton, B. W.; White, A. H. J. Chem. Soc., Chem. Commun. 1986,23,1722. (b) Byers, P. K.; Canty, A. J.; Crespo, M.; Puddephatt, R. J.; Scott, J. D. Organometallics 1988, 6, 1363. (c) Byers, P. K.; Canty, A. J. J. Chem. Soc., Chem. Commun. 1988, 639. (d) Catellani, M.; Chivsoli, G. P. J. Organomet. Chem. 1988, 346, C35. (e) Crespo, M.; Puddephatt, R. J. Organometallics 1988, 6, 2548.
15. Coulson. D. R. Inorg. Synth. 1972. 13. 121.
16. Doyle, J. R.; Slade, P. E.; Jonassen, H. B. Inorg. Synth. 1960, 6, 216.
17. Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549.
18. Goure, W. F.; Wright, M. E.; Davis, P. D.; Labadie, S. S.; Stille, J. K. J. Am. Chem. Soc. 1984. 106. 6417.
19. Loque. M. W.; Teng, K. J. Org. Chem. 1982. 47, 2549.
20. Yamamoto, Y.; Nishi, S.; Yamoda, J. J. Am. Chem. Soc. 1986,108, 7116.
21. Bogoradovskii, E. T.; Zavgorodnii, V. S.; Petrov, A. Zh. Obshcb. Khim. 1977. 1548.
22. Itahara, K. J. Org. Chem. 1985, 50, 5277.