Nickel catalyzed electrochemical heteroarylation of activated olefins

Synthesis

Volumn , Issue 12, 2002, Pages 1752-1758

  Condon, Sylvie ^a   Dupré, Daniel ^a   Lachaise, Isabelle ^a   Nédélec, Jean Yves ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

Alkenes; Catalysis; Electrochemistry; Heteroaryl halide; Nickel

Indexed keywords

ANODES; CATALYSIS; NICKEL; OLEFINS;

HETEROARYLATION;

ADDITION REACTIONS;

2 BROMOPYRIDINE; 2 BROMOTHIOPHENE; 2 CHLORO 6 METHYLOXYPYRIDINE; 2 CHLOROPYRIDINE; 2 CHLOROQUINOLINE; 2 CHLOROTHIOPHENE; 3 BROMOPYRIDINE; 3 BROMOQUINOLINE; 3 BROMOTHIOPHENE; 4 CHLORO 2 METHYLQUINOLINE; ALKENE DERIVATIVE; HALIDE; NICKEL; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ARYLATION; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0036989724     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-33654     Document Type: Article

References (28)

1. (a) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059.
2. (b) Turck, A.; Plé N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489.
3. (a) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron Lett. 1999, 40, 4339.
4. (b) Trécourt, F.; Breton, G.; Bonnet, V.; Mongin, F.; Marsais, F.; Quéguiner, G. Tetrahedron 2000, 56, 1349.
5. (c) Bérillon, L.; Leprêtre, A.; Turck, A.; Plé N.; Quéguiner, G.; Cahiez, G.; Knochel, P. Synlett 1998, 1359.
6. (d) Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449.
7. (a) Jetter, M. C.; Reitz, A. B. Synthesis 1998, 829.
8. (b) Turner, R. M.; Lindell, S. D. J. Org. Chem. 1991, 56, 5739.
9. Felding, J.; Kristensen, J.; Bjerregaard, T.; Sander, L.; Vedso, P.; Begtrup, M. J. Org. Chem. 1999, 64, 4196.
10. (a) Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M. Tetrahedron 1982, 38, 3347.
11. (b) Chi, S. M.; Choi, J. K.; Yum, E. K.; Chi, D. Y. Tetrahedron Lett. 2000, 41, 919.
12. (a) For homocoupling see: Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80.
13. (b) For conjugate addition reaction see: Sustmann, R.; Hopp, P.; Holl, P. Tetrahedron Lett. 1989, 30, 689.
14. Durandetti, M.; Nédélec, J. Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748.
15. Durandetti, M.; Périchon, J.; Nédélec, J. Y. Tetrahedron Lett. 1999, 40, 9009.
16. (a) Condon-Gueugnot, S.; Léonel, E.; Nédélec, J. Y.; Périchon, J. J. Org. Chem. 1995, 60, 7684.
17. (b) Condon, S.; Dupré, D.; Falgayrac, G.; Nédélec, J. Y. Eur. J. Org. Chem. 2002, 105.
18. (c) Condon-Gueugnot, S.; Dupré, D.; Nédélec, J. Y.; Périchon, J. Synthesis 1997, 1457.
19. (a) Cannes, C.; Condon, S.; Durandetti, M.; Périchon, J.; Nédélec, J. Y. J. Org. Chem. 2000, 65, 4575.
20. (b) Gosmini, C.; Lasry, S.; Nédélec, J. Y.; Périchon, J. Tetrahedron 1998, 54, 1289.
21. (c) Gosmini, C.; Nédélec, J. Y.; Périchon, J. Tetrahedron Lett. 2000, 41, 201.
22. (d) Durandetti, M.; Périchon, J.; Nédélec, J. Y. Tetrahedron Lett. 1997, 38, 8683.
23. (e) de França, K. W. R.; Navarro, M.; Léonel, E.; Durandetti, M.; Nédélec, J. Y. J. Org. Chem. 2002, 67, 1838.
24. Chaussard, J.; Folest, J. C.; Nédélec, J. Y.; Périchon, J.; Sibille, S.; Troupel, M. Synthesis 1990, 369.
25. Ferles, M.; Kafka, S.; Silhánková A.; Sputová, M. Collect. Czech. Chem. Commun. 1981, 46, 1167.
26. Wenkert, E.; Chang, C. J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645.
27. Tamaru, Y.; Yamada, Y.; Yoshida, Z. I. Tetrahedron 1979, 35, 329.
28. Griesgraber, G.; Kramer, M. J.; Elliot, R. L.; Nilius, A. M.; Ewing, P. J.; Raney, P. M.; Bui, M. H.; Flamm, R. K.; Chu, D. T. W.; Plattner, J. J.; Or, Y. S. J. Med. Chem. 1998, 41, 1660.