Promotion of reaction of N-H bonds with triarylbismuth and cupric acetate

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9013-9016

  Chan, Dominic M T ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; BISMUTH DERIVATIVE; CARBAMIC ACID DERIVATIVE; COPPER ACETATE; IMIDE; REAGENT; SULFONAMIDE; TERTIARY AMINE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS; TEMPERATURE;

EID: 0030577490     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02116-8     Document Type: Article

References (16)

1. 1. (a) Barton, D.H.R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1986, 27, 3615-3618;
2. (b) Barton, D.H.R.; Finet, J.-P.; Khamsi, Tetrahedron Lett. 1987, 28, 887-890.
3. 2. Barton, D.H.R.; Ozbalik, N.; Ramesh, M. Tetrahedron Lett. 1988, 29, 857-860.
4. 3. For an overview, see: Finet, J.-P. Chem. Rev. 1989, 89, 1487-1501.
5. 4. Barton, D.H.R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1989, 30, 937-940.
6. 5. Banfi, A.; Bartoletti, M.; Bellora, E.; Bignotti, M.; Turconi, M. Synthesis, 1994, 775-776.
7. 6. Barton, D.H.R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1988, 29, 1115-1118.
8. 2 system has been shown by Barton to be highly dependent on the basicity of the amine substrate, e.g., n-butylamine gave a good yield of the N-phenylated derivatives but p-nitroaniline reacted poorly. See ref. 1b.
9. 8. Barton, D.H.R.; Finet, J.-P.; Motherwell, W.B.; Pichon, C. J. Chem. Soc., Perkin Trans. I, 1987, 251-259.
10. 9. Barton, D.H.R.; Blazejewski, J.-C.; Charpiot, B.; Lester, D.J.; Motherwell, W.B.; Barros Papoula, M.T. J. Chem. Soc., Chem. Commun. 1980, 827-829.
11. 10. Akhtar, M.S.; Brouillette, W.J.; Waterhous, D.V. J. Org. Chem. 1990, 55, 5222-5225.
12. 3. See ref. 5 for examples and a typical procedure. For a discussion on preparation of various triarylbismuth compounds, see: Barton, D.H.R.; Bhatnagar, N.Y.; Finet, J.-P.; Motherwell, W.B. Tetrahedron, 1986, 42, 3111-3122.
13. 4.
14. 13. Coppola, G.M. J. Heterocydic Chem., 1987, 24, 1249-1251.
15. 14. For a discussion on the reaction mechanism of the Cu-mediated bismuth N-arylation, see reference 1b.
16. 2 could be added during the course of the reaction to ensure complete conversion of the substrate.