Selectivity in the tandem cyclization - Carboxylation reaction of unsaturated haloaryl ethers catalyzed by electrogenerated nickel complexes

European Journal of Organic Chemistry

Volumn , Issue 8, 1999, Pages 1885-1891

  Olivero, S ^a   Dunach E ^a  

^a CNRS   (France)

Author keywords

Carbon dioxide fixation; Cyclizations; Dihydrobenzofuran; Electrochemistry; Nickel

Indexed keywords

BENZOFURAN DERIVATIVE; CARBON DIOXIDE; ETHER DERIVATIVE; NICKEL COMPLEX;

ARTICLE; CARBOXYLATION; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ELECTROCHEMISTRY; MOLECULAR INTERACTION; REACTION ANALYSIS; REDUCTION;

EID: 0345035476     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199908)1999:8<1885::aid-ejoc1885>3.0.co;2-u     Document Type: Article

References (36)

1. S. Olivero, E. Duñach, Tetrahedron Lett. 1995, 36, 4429-32.
2. T. Eicher, S. Hauptmann, in The Chemistry of Heterocycles, Thieme, Organic Chemistry, Monograph Series, Stuttgart, 1995.
3. X. Guan, R. T. Borchardt, Tetrahedron Lett. 1994, 35, 3013-3016.
4. [4a] S. Inoue, N. Yamazaki, in Organic and Bio-Organic Chemistry of Carbon Dioxide, Kodansha Ltd., Tokyo, 1992.
5. 4[b] A. Behr, in Carbon Dioxide Activation by Metal Complexes, VCH, Weinheim, 1988.
6. [5a] K. Shankaran, C. P. Sloan, V. Sniekus, Tetrahedron Lett. 1985, 26, 6001-6004.
7. [5b] A. J. L. Beckwith, W. B. Gara, J. Chem. Soc., Perkin Trans. 2 1975, 795-802.
8. [6a] D. P. Curran, M. J. Totleben, J. Am. Chem. Soc. 1992, 114, 6050-6058.
9. [6b] G. A. Molander, L. S. Harring, J. Org. Chem. 1990, 55, 6171.
10. [6c] J. Inanaga, O. Ujikawa, M. Yamaguchi, Tetrahedron Lett. 1991, 32, 1737-1740.
11. [7a] V. F. Patel, G. Pattenden, J. Chem. Soc., Chem. Commun. 1987, 871-872.
12. [7b] T. Inokuchi, H. Kawafuchi, K. Aoki, A. Yoshida, S. Torii, Bull. Chem. Soc. Jpn. 1994, 67, 595-598.
13. [7c] S. Busato, R. Scheffold, Helv. Chim. Acta 1994, 77, 92-99.
14. [8a] S. Ozaki, H. Matsushita, H. Ohmori,. J. Chem. Soc., Chem. Commun. 1992, 1120-1121.
15. [8b] S. Ozaki, I. Horiguchi, H. Matsushita, H. Ohmori, Tetrahedron Lett. 1994, 35, 725-728.
16. 2 has been reported in a symposium: H. Tanaka, O. Ren, S. Torii, 2nd Intern. Symposium on Electroorganic Synthesis, Kurashiki, Japan, 1994.
17. M. Beley, J. P. Collin, R. Ruppert, J. P. Sauvage, J. Am. Chem. Soc. 1986, 108, 7461-7467.
18. B. P. Sullivan, in Electrochemical and Electrocatalyticat Reactions of Carbon Dioxide, Elsevier, Amsterdam, chapter 5, 1993.
19. [12a] O. Sock, M. Troupel, J. Périchon, Tetrahedron Lett. 1985, 26, 1509-1512.
20. [12b] G. Silvestri, S. Gambino, G. Filardo, G. Greco, A. Gulotta, Tetrahedron Lett. 1984, 25, 4307-4310.
21. [13a] C. Amatore, A. Jutand, J. Am. Chem. Soc. 1991, 113, 2819-2825.
22. [13b] J. F. Fauvarque, C. Chevrot, A. Jutand, M. Francois, J. Perichon, J. Organomet. Chem. 1984, 264, 273-281.
23. S. Dérien, E. Duñach, J. Périchon, J. Am. Chem. Soc. 1991, 113, 8447-8454.
24. S. Dérien J. C. Clinet, E. Duñach, J. Périchon, Tetrahedron 1992, 48, 5235-5248.
25. J. Chaussard, J. C. Folest, J. Y. Nédélec, J. Périchon, S. Sibille, M. Troupel, Synthesis 1990, 5, 369-387.
26. G. Silvestri, S. Gambino, G. Filardo, Acta Chem. Scand. 1991, 987-992.
27. 2] catalyst, a stable pink complex, was easily prepared from nickel bromide and cyclam in absolute ethanol: B. Bosnich, C. K. Poon, M. L. Tobes, Inorg. Chem. 1965, 4, 1102-1104.
28. S. Olivero, E. Duñach, J. Chem. Soc., Chem. Commun. 1995, 2497-2498.
29. [20a] C. Gosden, K. P. Healy, D. Pletcher, J. Chem. Soc., Dalton Trans. 1978, 972-976.
30. [20b] C. Gosden, D. Pletcher, J. Organomet. Chem. 1980, 186, 401-409.
31. [20c] K. P. Healy, D. Pletcher, J. Organomet. Chem. 1978, 161, 109-120.
32. S. Olivero, J. P. Rolland, E. Dun̂ach, Organometallics 1998, 17, 3747-3753.
33. R. Rai, D. B. Collum, Tetrahedron Lett. 1994, 35, 6221-6224.
34. S. C. Zimmerman, K. D. Cramer, A. A. Galan, J. Org. Chem. 1989, 54, 1256-1264.
35. A. N. Abeywickrema, A. L. J. Beckwith, S. Gerba, J. Org. Chem. 1987, 52, 4072-4078.
36. A. R. Deshpande, M. V. Paradkar, Synth. Commun. 1990, 20, 809-816.