Nucleophilic Aromatic Substitution by Organoaluminum Reagents. Application to the Synthesis of Indoles

Journal of the American Chemical Society

Volumn 105, Issue 24, 1983, Pages 7177-7179

  Fujiwara, Junya ^a   Fukutani, Yoshimi ^a   Sano, Hiromi ^a   Maruoka, Keiji ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000762979     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00362a030     Document Type: Article

References (9)

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2. For reviews of classical nucleophilic aromatic substitution, see: Bunnett, J. F.; Zahler, R.E. Chem. Rev. 1951, 49, 273. Hughes, E. D.; Ingold, C. K. Quart. Rev. (London) 1952, 6, 34. Bunnett, J. F. Quart. Rev. (London) 1958, 12, 1. Sauer, R.; Huisgen, R. Angew. Chem. 1960, 72, 294. Ross, S. D. Progr. Phys. Org. Chem. 1963, 1, 31.
3. Nucleophilic aromatic alkylation of anilines and its applications to natural product synthesis: Gassman, P. G.; Gruetzmacher, G.; Smith, R. H. Tetrahedron Lett. 1972, 497. Johnson, C. R.; Bacon, C. C.; Kingsbury, W. D. Tetrahedron Lett. 1972, 501. Gassman, P. G.; Gruetzmacher, G. J. Am. Chem. Soc. 1973, 95, 588. Gassman, P. G.; Drewes, H. R. J. Am. Chem. Soc. 1974, 96, 3003. Gassman, P. G.; Gruetzmacher, G. J. Am. Chem. Soc. 1974, 96, 5487. Gassman, P. G.; van Bergen, T. J.; Gilbert, D. P.; Cue, B. W. J. Am. Chem. Soc. 1974, 96, 5495. Gassman, P. G.; van Bergen, T. J.; Gruetzmacher, G. J. Am. Chem. Soc. 1974, 96, 5512.
4. For reviews of nucleophilic alkylation of arene-metal complexes, see: Semmelhack, M. F. Ann. N. Y. Acad, Sci. 1977, 295, 36. Jaouen, G. In “Transition Metals Organometallics in Organic Synthesis”; Alper, H., Ed.; Academic Press: New York, 1978; p. 65. Semmelhack, M. F. In “Organic Synthesis. Today and Tomorrow”; Trost, B. M., Hutchinson, C. R., Eds.; Pergamon Press: New York, 1981; p. 63. See also: Semmelhack, M. F.; Zask, A. J. Am. Chem. Soc. 1983, 105, 2034.
5. Julia, M.; Le Goffic, F.; Igolen, J.; Braillage, M. Tetrahedron Lett. 1969, 1569. Ohta, T.; Machida, R.; Takeda, K.; Endo, Y.; Shudo, K.; Okamoto, T. J. Am. Chem. Soc. 1980, 102, 6385. Endo, Y.; Shudo, K.; Okamoto, T. J. Am. Chem. Soc. 1982, 104, 6393.
6. Kamm, O. Org. Synth. 1941, 1, 445.
7. For chemistry of anilenium ions, see: Gassman, P. G.; Campbell, G. A.; Frederick, R.C. J. Am. Chem. Soc. 1972, 94, 3884. Gassman, P. G.; Campbell, G. A. J. Am. Chem. Soc. 1972, 94, 3891, and references cited therein.
8. Castro, C. E.; Gaughan, E. J.; Owsley, D.C. J. Org. Chem. 1966, 31, 4071. Addition of CaC03 improved the yield of the reaction.
9. Julia, M.; Manoury, P.; Igolen, J.C.R. Hebd. Seances Acad. Sci. 1960, 251, 394.