Triarylbismuthane - Iodobenzene diacetate: One-pot system for copper- catalysed N-arylation under neutral conditions

Tetrahedron

Volumn 54, Issue 17, 1998, Pages 4313-4318

  Combes, Sébastien ^a   Finet, Jean Pierre ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH DERIVATIVE;

ARTICLE; CATALYSIS; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032560096     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00126-4     Document Type: Article

References (30)

1. 1. Sax Irving, N. Dangerous Properties of Industrial Materials; Van Nostrand Rheinhold: New York, 1989.
2. 2. Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis 1997, 249-267.
3. 3. a) Barton, D.H.R.; Finet, J.-P. Pure Appl. Chem. 1987, 59, 937-946;
4. b) Abramovitch, R.A.; Barton, D.H.R.; Finet, J.-P. Tetrahedron 1988, 44, 3039-3071;
5. c) Finet, J.-P. Chem. Rev. 1989, 89, 1487-1501;
6. d) Freedman, L.D.; Doak, G.O. in The Chemistry of the Metal-Carbon Bond; Hartley, F.R., Ed.; J. Wiley & Sons: New York, 1989; Vol. 5, Ch. 9, pp. 397-433.
7. 4. Sinclair, P.J.; Wong, F.; Wyvratt, M.; Staruch, M.J.; Dumont, F. Bioorg. Med. Chem. Lett. 1995, 5, 1035-1038.
8. 5. Sinclair, P.J.; Wong, F.; Staruch, M.J.; Wiederrecht, G.; Parsons, W.H.; Dumont, F.; Wyvratt, M. Bioorg. Med. Chem. Lett. 1996, 6, 2193-2196.
9. 6. a) Finet, J.-P. Triphenylbismuth diacetate in Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A., Ed.; J. Wiley and Sons: New York, 1995; Vol. 8, pp. 5344-5345;
10. b) Dodonov, V.A.; Gushchin, A.V. Izv. Akad. Nauk, Ser. Khim. 1993, 2043-2047; Russ. Chem. Bull. 1993, 42, 1955-1959.
11. b) Dodonov, V.A.; Gushchin, A.V. Izv. Akad. Nauk, Ser. Khim. 1993, 2043-2047; Russ. Chem. Bull. 1993, 42, 1955-1959.
12. 7. a) David, S.; Thieffry, A. J. Org. Chem. 1983, 48, 441-447;
13. b) Barton, D.H.R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1986, 27, 3615-3618;
14. c) Barton, D.H.R.; Finet, J.-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622.
15. 8. For some recent applications: a) Brunner, H.; Chuard, T. Monatsh. Chem. 1994, 125, 1293-1300;
16. b) Harada, T.; Ueda, S.; Yoshida, T.; Inoue, A.; Takeuchi, M.; Ogawa, N.; Oku, A.; Shiro, M. J. Org. Chem. 1994, 59, 7575-7576;
17. c) Srivastava, R.P.; Zhu, X.; Walker, L.A.; Sindelar, R.D. Bioorg. Med. Chem. Lett. 1995, 5, 2429-2434.
18. 9. Goel, R.G.; Prasad, H.S. Can. J. Chem. 1970, 48, 2488-2493.
19. 10. Barton, D.H.R.; Kitchin, J.P.; Lester, D.J.; Motherwell, W.B.; Papoula, M.T.B. Tetrahedron 1981, 37, Suppl. 1, 73-79.
20. 11. Wittig, G.; Hellwinkel, D. Chem. Ber. 1964, 97, 789-793.
21. 12. Pichon, C., Doctorat d'Etat ès Sciences, Université de Paris-Sud Orsay, 1985.
22. 13. Dodonov, V.A.; Gushchin, A.V.; Brilkina, T.G. Zh. Obshch. Khim. 1985, 55, 73-80.
23. 14. Arnauld, T.; Barton, D.H.R.; Doris, E. Tetrahedron 1997, 53, 4137-4144.
24. 15. Combes, S.; Finet, J.-P. Synth. Commun. 1996, 26, 4569-4575.
25. 16. Wieber, M. Gmelin Handbuch der Anorganische Chemie; Springer-Verlag: Berlin, 1977; Band 47, Bismut-Organische Verbindungen, p. 38.
26. 17. Imazaki, H.; Fujikawa, M.; Konishi, T.; Kawaguchi, Y. JP 63,174,926 (Chem. Abstr. 1989, 111, 154111j).
27. 18. Moffett, R.B.; Aspergren, B.D. J. Am. Chem. Soc. 1960, 82, 1600-1607.
28. 19. Buu-Hoi, N.P. J. Chem. Soc. 1949, 670-676.
29. 20. Suzuki, H.; Ikegami, T.; Azuma, T. J. Chem. Soc., Perkin Trans. 1 1997, 1609-1616.
30. 21. Dodonov, V.A.; Gushchin, A.V.; Brilkina, T.G. Zh. Obshch. Khim. 1985, 55, 2514-2519.