A general and convenient procedure for the synthesis of N- alkylarylamines and N-alkylheteroarylamines by electrophilic amination of cuprates with N-alkylhydroxylamines

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 641-643

  Bernardi, Paolo ^a   Dembech, Pasquale ^b   Fabbri, Gaia ^a   Ricci, Alfredo ^a   Seconi, Giancarlo ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033593396     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981412h     Document Type: Article

References (31)

1. Suga, K.; Watanabe, S.; Fujita, T.; Pan, T. P. Bull. Chem. Soc. Jpn. 1969, 42, 3606-3608.
2. Slota, K. H.; Franke, W. Ber. Dtsch. Chem. Ges. 1930, 63, 678-691.
3. Hashimoto, S.; Furukawa, I. Kogyo Kagaku Zasshi 1967, 70, 177-179 (Chem. Abstr. 1967, 67, 116663f).
4. Hashimoto, S.; Furukawa, I. Kogyo Kagaku Zasshi 1967, 70, 177-179 (Chem. Abstr. 1967, 67, 116663f).
5. Kametani, T.; Kigasawa, K.; Hayasaka T. Yakugaku Zasshi 1968, 88, 445-452 (Chem. Abstr. 1968, 69, 106477o).
6. Kametani, T.; Kigasawa, K.; Hayasaka T. Yakugaku Zasshi 1968, 88, 445-452 (Chem. Abstr. 1968, 69, 106477o).
7. Lewis, W. W., Jr. U.S. Patent 2,541,655, 1951 (Chem. Abstr. 1952, 46, 3565a).
8. Radakrishna Murti, P. S.; Panigrahi, G. P. J. Indian Chem. Soc. 1969, 46, 567-569.
9. (a) Petigara, R. B.; Yale, H. L. J. Heterocycl. Chem. 1974, 11, 331-337.
10. (b) Beak, P.; Lee, J.; McKinnie, B. G. J. Org. Chem. 1978, 43, 1367-1372.
11. Binder, D.; Habison, G.; Noe, C. R. Synthesis 1977, 255-256.
12. (a) Gupton, J. T.; Idoux, J. P.; Baker, G.; Colon, C.; Crews, A. D.; Jurss, C. D.; Rampi, R. C. J. Org. Chem. 1983, 48, 2933-2936.
13. (b) Wickam, P. P.; Hazen, K. H.; Guo, H.; Jones, G.; Reuter, K. H.; Scott, W. J. J. Org. Chem. 1991, 56, 2045-2050.
14. (c) Ibata, T.; Isogami, Y.; Toyoda. J. Bull. Chem. Soc. Jpn. 1991, 64, 42-49.
15. (d) Bhaskar, Kanth, J. V.; Periasamy, M. J. Org. Chem. 1993, 58, 3156-3157.
16. Louie, G.; Driver, M. S.; Hammann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273.
17. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
18. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066-6068 and references therein.
19. Casarini, A.; Dembech, P.; Lazzari, D.; Marini, E.; Reginato, G.; Ricci, A.; Seeoni G. J. Org. Chem. 1993, 58, 5620-5623.
20. Unpublished results.
21. (a) Alberti, A.; Canè, F.; Dembech, P.; Lazzari, D.; Ricci, A.; Seconi, G. J. Org. Chem. 1996, 61, 1677-1681.
22. (b) Canè, F.; Brancaleoni, D.; Dembech, P.; Ricci, A.; Seconi, G. Synthesis 1997, 545-548.
23. Smrekar, O.; Wannagat, U. Monatsh. Chem. 1969, 100, 760-765.
24. Krishnamurty, S. Tetrahedron Lett. 1982, 23, 3315-3318.
25. Juaristi, E.; Reyna, J. D. Tetrahedron Lett. 1984, 25, 3521-3524.
26. Botta, M.; De Angelis, F.; Nicoletti, R. Synthesis 1997, 722-723.
27. Gage, J. R.; Wagner, J. M. J. Org. Chem. 1995, 60, 2613-2614.
28. Katritzky, A. R.; Rachwal, S.; Rachwal, B. J. Chem. Soc., Perkin Trans, 1 1987, 805-809.
29. Kawasaki, M.; Suzuki, Y.; Terashima, S. Chem. Lett. 1984, 239-242.
30. Katritzky, A. R.; Vanden Eynde J.-J. J. Chem. Soc., Perkin Trans, 1 1989, 639-642.
31. Gilman, H.; Haubein, A. H. J. Am. Chem. Soc. 1944, 66, 1515-1516.