Short step synthesis of 4-substituted indoles using palladium-catalyzed C-C bond forming reaction

Heterocycles

Volumn 42, Issue 1, 1996, Pages 113-116

  Doi, Kazuyuki ^a   Mori, Miwako ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001684664     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s34     Document Type: Article

References (11)

1. For the review of the synthesis of 4-substituted indoles, see A. P. Kozikowski, Heterocycles, 1981, 16, 267; I. Ninomiya and T. Kiguchi in "The Alkaloids", Ed. A. Brossi, Academic Press, 1990, 38, 1.
2. For the review of the synthesis of 4-substituted indoles, see A. P. Kozikowski, Heterocycles, 1981, 16, 267; I. Ninomiya and T. Kiguchi in "The Alkaloids", Ed. A. Brossi, Academic Press, 1990, 38, 1.
3. For the recent synthetic methods of 4-substituted indoles, see J. H. Tidwell, A. J. Peat, and S. L. Buchwald, J. Org. Chem., 1994, 59, 7164; H, Ishibashi, S. Akamatsu, H. Iriyama, and M. Ikeda, Chem. Pharm. Bull., 1994, 42, 2450; M. Fuji, H. Muratake, and M. Natsume, Chem. Pharm. Bull., 1992, 40, 2338; M. E. Krolski, A. F. Renaldo, D. E. Rudisill, and J. K. Stille, J. Org. Chem., 1988, 53, 1170.
4. For the recent synthetic methods of 4-substituted indoles, see J. H. Tidwell, A. J. Peat, and S. L. Buchwald, J. Org. Chem., 1994, 59, 7164; H, Ishibashi, S. Akamatsu, H. Iriyama, and M. Ikeda, Chem. Pharm. Bull., 1994, 42, 2450; M. Fuji, H. Muratake, and M. Natsume, Chem. Pharm. Bull., 1992, 40, 2338; M. E. Krolski, A. F. Renaldo, D. E. Rudisill, and J. K. Stille, J. Org. Chem., 1988, 53, 1170.
5. For the recent synthetic methods of 4-substituted indoles, see J. H. Tidwell, A. J. Peat, and S. L. Buchwald, J. Org. Chem., 1994, 59, 7164; H, Ishibashi, S. Akamatsu, H. Iriyama, and M. Ikeda, Chem. Pharm. Bull., 1994, 42, 2450; M. Fuji, H. Muratake, and M. Natsume, Chem. Pharm. Bull., 1992, 40, 2338; M. E. Krolski, A. F. Renaldo, D. E. Rudisill, and J. K. Stille, J. Org. Chem., 1988, 53, 1170.
6. For the recent synthetic methods of 4-substituted indoles, see J. H. Tidwell, A. J. Peat, and S. L. Buchwald, J. Org. Chem., 1994, 59, 7164; H, Ishibashi, S. Akamatsu, H. Iriyama, and M. Ikeda, Chem. Pharm. Bull., 1994, 42, 2450; M. Fuji, H. Muratake, and M. Natsume, Chem. Pharm. Bull., 1992, 40, 2338; M. E. Krolski, A. F. Renaldo, D. E. Rudisill, and J. K. Stille, J. Org. Chem., 1988, 53, 1170.
7. M. Matsumoto and N. Watanabe, Heterocycles, 1984, 22, 2313.
8. 1H-nmr and COSY spectra.
9. N-Tosyl group could be deprotected by sodium hydroxide in alcoholic solvent if desired.
10. G. T. Crisp, W. J. Scott, and J. K. Stille, J. Am. Chem. Soc., 1984, 106, 7500.
11. T. Oh-e, N. Miyaura, and A. Suzuki, Synlett, 1990, 221.