Direct electroreductive preparation of indolines and indoles from diazonium salts

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2735-2738

  LeStrat, Franck ^a   Murphy, John A ^a   Hughes, Mark ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

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ARTICLE;

EID: 0042190315     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0262643     Document Type: Article

References (24)

1. See special issue: Pure Appl. Chem. 2000, 72, 1207-1403.
2. For a review, see: Eberson, L.; Schäfer, H. Fortschr. Chem. Forsch, 1971, 21, 5.
3. Olivero, S.; Clinet, J. C.; Dunach, E. Tetrahedron Lett. 1995, 36, 4429.
4. Grimshaw, J.; Trocha-Grimshaw, J. Tetrahedron Lett. 1974, 15, 993. Grimshaw, J.; Hamilton, R.; Trocha-Grimshaw, J. J. Chem. Soc., Perkin Trans. 1 1982, 229. Grimshaw, J.; Haslett, R. J.; Trocha-Grimshaw, J. J. Chem. Soc. Perkin Trans. 1 1977, 2448.
5. Grimshaw, J.; Trocha-Grimshaw, J. Tetrahedron Lett. 1974, 15, 993. Grimshaw, J.; Hamilton, R.; Trocha-Grimshaw, J. J. Chem. Soc., Perkin Trans. 1 1982, 229. Grimshaw, J.; Haslett, R. J.; Trocha-Grimshaw, J. J. Chem. Soc. Perkin Trans. 1 1977, 2448.
6. Grimshaw, J.; Trocha-Grimshaw, J. Tetrahedron Lett. 1974, 15, 993. Grimshaw, J.; Hamilton, R.; Trocha-Grimshaw, J. J. Chem. Soc., Perkin Trans. 1 1982, 229. Grimshaw, J.; Haslett, R. J.; Trocha-Grimshaw, J. J. Chem. Soc. Perkin Trans. 1 1977, 2448.
7. Gottlieb, R.; Neumeyer, J. L. J. Am. Chem. Soc. 1976, 98, 7108.
8. Munusamy, R.; Dhathathreyan, K. S.; Balasubramanian, K. K.; Venkatachalam, C. S. J. Chem. Soc., Perkin Trans. 2 2001, 1154.
9. Ozaki, S.; Matsushita, H.; Ohmori, H. J. Chem. Soc., Chem. Commun. 1992, 1121. Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725. Clinet, J. C.; Dunach, E. J. Organomet. Chem., 1995, 503, C48.
10. Ozaki, S.; Matsushita, H.; Ohmori, H. J. Chem. Soc., Chem. Commun. 1992, 1121. Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725. Clinet, J. C.; Dunach, E. J. Organomet. Chem., 1995, 503, C48.
11. Ozaki, S.; Matsushita, H.; Ohmori, H. J. Chem. Soc., Chem. Commun. 1992, 1121. Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725. Clinet, J. C.; Dunach, E. J. Organomet. Chem., 1995, 503, C48.
12. Elofson, R. M.; Edsberg, R. L.; Mecherly, P. J. Electrochem. Soc. 1950, 97, 166. Elofson, R. M.; Gadallah, F. F. J. Org. Chem. 1969, 34 854.
13. Elofson, R. M.; Edsberg, R. L.; Mecherly, P. J. Electrochem. Soc. 1950, 97, 166. Elofson, R. M.; Gadallah, F. F. J. Org. Chem. 1969, 34 854.
14. Atkinson, E. R.; Warren, H. H.; Abell, P. I.; Wing, R. E. J. Am. Chem. Soc. 1950, 72, 915. Atkinson, E. R.; Garland, C. E.; Butler, A. F. J. Am. Chem. Soc. 1953, 75, 983.
15. Atkinson, E. R.; Warren, H. H.; Abell, P. I.; Wing, R. E. J. Am. Chem. Soc. 1950, 72, 915. Atkinson, E. R.; Garland, C. E.; Butler, A. F. J. Am. Chem. Soc. 1953, 75, 983.
16. Kochi, J. K. J. Am. Chem. Soc. 1955, 77, 3208.
17. Elofson, R. M.; Gadallah, F. F. J. Org. Chem. 1971, 36, 1769. Gadallah, F. F.; Cantu, A. A.; Elofson, R. M. J. Org. Chem. 1973, 38, 2386.
18. Elofson, R. M.; Gadallah, F. F. J. Org. Chem. 1971, 36, 1769. Gadallah, F. F.; Cantu, A. A.; Elofson, R. M. J. Org. Chem. 1973, 38, 2386.
19. Patro B.; Merrett, M. C.; Makin, S. D.; Murphy, J. A.; Parkes, K. E. B. Tetrahedron Lett. 2000, 41, 421.
20. Minisci, F.; Coppa, F.; Fontana, F.; Pinese, G.; Zhao, L.; J. Org. Chem. 1992, 57, 3929.
21. We thank Professor W. R. Bowman for this suggestion.
22. Murphy, J. A.; Scott, K. A.; Sinclair, K. A.; Martin, C. G.; Kennedy, A. R.; Lewis, N. J. Chem. Soc., Perkin Trans. 1 2000, 2395 and ferences therein.
23. (a) Freidlina, R. Kh.; Terent'ev, A. B. Adv. Free Radical Chem., 1980, 6, 1.
24. (b) Freidlina, R. Kh. Adv. Free Radical Chem. 1965, 1, 211.