Lithium and potassium bis(trimethylsilyl)amide: Utilizing non-nucleophilic bases as nitrogen sources

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3187-3188

  Brüning, Jörg ^a  

^a Callery Chemical Company   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLAMINE DERIVATIVE;

AMINATION; ARTICLE; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0343035705     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00608-4     Document Type: Article

References (16)

1. Commercially available in bulk quantities from Callery Chemical Company.
2. Rathman, T.L. Chem. Spec. 1989, 9(5). 300-306.
3. (a) Rühlmann, K. Chem. Ber. 1961, 94, 2311-2313.
4. (b) Zeiss, W.; Feldt, C.; Weis, J. Chem. Ber. 1978, 111, 1180-1194
5. (c)Bestmann, H. J.; Wölfel, G. Chem. Ber. 1984, 117, 1250-1254.
6. (d)Bestmann, H. J.; Wölfel, G. Angew. Chem., Int. Ed. Engl. 1984, 23(1), 53.
7. (e) Refvik, M. D.; Schwan, A. L. J. Org. Chem. 1996, 61,4232-4239.
8. Mantri, P.; Duffy, D. E.; Kettner, C. A. K. J. Org. Chem. 1996, 61, 5690-5692.
9. For silver iodide mediated aminations of allylic chlorides with lithium bis(trimethylsilyl)amide see: Murai, T.; Yamamoto, M.; Kondo, S.; Kato, S. J. Org. Chem. 1993, 58, 7440-7445.
10. Heck, R.F. Palladium Reagents in Organic Synthesis, Academic Press 1985, pp. 122-130
11. For an example of lithium bis(trimethylsilyl)amide as a hindered base in palladium(0) catalyzed aminations of arylbromides see: Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1996, 36(21), 3609-3612.
12. 3) ppm
13. The lower isolated yield was attributed partially to codistillation of allylHMDS with the reaction solvent toluene and decomposition during distillation. Based on GC analysis of the crude reaction mixture, no significant hydrolysis occured during the aqueous workup.
14. Binger, P.; Wedemann, P.; Goddard, R.; Brinker ,U.H. J. Org Chem. 1996, 61, 6462-6464.
15. (a) Von Matt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T.; Helmchen, G. Tetrahedron: Asymmetry 1994, 5(4), 573-584.
16. (b) Jumnah, R.; Williams, A. C.; Williams, J. M. J. Synlett 1995(8), 821.