A convenient synthesis of 3,6-substituted carbazoles via nickel catalyzed cross-coupling

Tetrahedron

Volumn 54, Issue 42, 1998, Pages 12707-12714

  Park, Minnie ^a   Buck, Jason R ^a   Rizzo, Carmelo J ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

Corriu Kumada Cross coupling reaction; Grignard reagents; Polycyclic heterocyclic compounds

Indexed keywords

CARBAZOLE DERIVATIVE; NICKEL;

ARTICLE; CATALYSIS; CATALYST; METAL BINDING; PRIORITY JOURNAL; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032532256     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00786-8     Document Type: Article

References (34)

1. 1. Saito, I.; Ikehira, H.; Kasatani, R.; Watanabe, M.; Matsuura, T.; J. Am. Chem. Soc. 1986, 108, 3115-3117.
2. 2. Prudhomme, D.R.; Wang, Z.; Rizzo, C. J.; J. Org. Chem. 1997, 62, 8257-8260.
3. 3. Ambrose, J. F.; Nelson, R. F.; J. Electrochem, Soc. 1968, 115, 1159-1164
4. 4. Ambrose, J. F.; Carpenter, L. L.; Nelson, R. F.; J. Electrochem. Soc. 1975, 122, 876-894.
5. 5. Buu-Hoï, N. P.; Hoán, N.; J. Am. Chem. Soc. 1951, 73, 98-100.
6. 6. Buu-Hoï, N. P.; Hoán, N.; J. Org. Chem. 1951, 16, 1327-1332.
7. 7. Kumada, M. Pure Appl. Chem. 1980, 52, 669-679.
8. 8. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M.; Bull Chem. Soc. Jpn. 1916, 49, 1958-1969.
9. 9. Gilman, H.; Spatz, S.M.; J. Am. Chem. Soc. 1941, 63, 1553-1557.
10. 10. Davis, F. A.; Mancinelli, P. A.; Balasubramanian, K.; Nadir, U.K.; J. Am. Chem. Soc. 1979, 101, 1044-1045.
11. 11. Hsieh, B. R.; Litt, M. H.; Macromolecules 1986, 19, 516-520.
12. 12. Nahm, S.; Weinreb S. M.; Tetrahedron Lett. 1981, 22, 3815-3818.
13. 13. Buu-Hoï, N. P.; Hoán N.; J. Org. Chem. 1950, 75, 123-130.
14. 14. Domanski, A.; Kyziol J. B.; Pol. J. Chem. 1985, 59, 613-620.
15. 15. Hidai, M.; Hikita, T.; Wada, T.; Fujikura, Y.; Uchida, Y.; Bull Chem. Soc. Jpn. 1975, 48, 2075-2077.
16. 16. Hidai M, Kokura K, Uchida Y. J. Organometal. Chem. 1973: 52, 431-434.
17. 17. Chakraborty, R.K.; Roy, S.; Prog. Chem. Org. Natur. Prod. 1991, 57, 71-152.
18. 18. Joule, J. A.; Adv. Heterocycl. Chem. 1984, 55, 83-198.
19. 19. Hoegl, H.; J. Phys. Chem. 1965, 69, 755-766.
20. 20. Zhang, Y.; Wang, L.; Wada, T.; Sasabe, H.; Polym. Sci. Part A, Polym. Chem. 1996, 34, 1359-1363 and references therein.
21. 21. Kuroki, M.; Tsunashima, Y.; J. Heterocyclic Chem. 1981, 18, 709-714.
22. 22. Tamura, M.; Kochi, J.; J. Am. Chem. Soc. 1971, 93, 1483-1485.
23. 23. Corriu, R. J. P.; Masse, J. P.; J. Chem. Soc. Chem. Commun. 1972, 144.
24. 24. Tamao, K.; Sumitani, K.; Kumada, M.; J. Am. Chem. Soc. 1972, 94, 4347-4376.
25. 25. Kovaleva, L. F.; Reutova, O. I.; Sarycheva, T. A.; Sheludyakov, O. A.; Novikov, A. N.; Filimonov, V. D.; J. Org. Chem. USSR 1988, 24, 583-585.
26. 26. Buu-Hoï, N. P.; Hoán, N.; Rec. Trav. Chim. Pays-Bas 1947, 66, 533-543.
27. 27. Knölker, H-J.; "Transition Metal-Mediated Synthesis of Carbazole Derivatives." In Advances in Nitrogen Heterocycles, Moody, CJ., Ed. JAI Press,: Greenwich, CT, 1995; vol. 1, pp. 173-204.
28. 28. Knölker, H-J.; Fröhner, W.; Wagner, A.; Tetrahedron Lett. 1998, 39, 2947-2950.
29. 29. Knölker, H-J.; Fröhner, W.; Tetrahedron Lett. 1998, 39, 2537-2540.
30. 30. Knölker, H-J.; Fröhner, W.; Synlett 1997, 1108-1110.
31. 31. Booth, G.; Chatt, J.; J. Chem. Soc. 1965, 3238-3241.
32. 32. Smith, K.; James, D.M.; Mistry, A. G.; Bye, M. R.; Faulkner, D. J.; Tetrahedron 1992, 48, 7479-7488.
33. 33. Haarer, D.; Meyer, H.; Strohriegl, P.; Makromol. Chem. 1991, 192, 617-629.
34. 34. Lopatinskii, V. P.; Sirotkina, E. E.; Anosova, M. M.; Chem. Abst. 1965, 63, 565d.