Nickel-catalyzed electrochemical coupling of aryl, heteroaryl or vinyl halides with activated alkyl chlorides: Synthetic and stereochemical aspects

Synthesis

Volumn , Issue 18, 2004, Pages 3079-3083

  Durandetti, Muriel ^a   Périchon, Jacques ^a  

^a CNRS   (France)

Author keywords

Aryl Halides; C C coupling; Electrochemistry; Nickel; Vinyl Halides

Indexed keywords

CATALYSIS; ELECTROCHEMISTRY; NICKEL; STEREOCHEMISTRY;

ALKYL HALIDES; ELECTROSYNTHESIS; HETEROARYLS; VINYL HALIDES;

AROMATIC COMPOUNDS;

ALKYL GROUP; CHLORIDE; HALIDE; NICKEL; VINYL DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; METAL BINDING; SHORT SURVEY; STEREOCHEMISTRY; SYNTHESIS;

EID: 11144325589     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834896     Document Type: Short Survey

References (40)

1. Nédélec, J. Y.; Périchon, J.; Troupel, M. Topics in Current Chemistry; Springer-Verlag: Berlin / Heidelberg, 1997, 185.
2. Rollin, Y.; Troupel, M.; Tuck, D.; Périchon, J. J. Organomet. Chem. 1986, 303, 131.
3. (a) Schlegel, B.; Hänel, F.; Gollmick, F. A.; Saluz, H.-P.; Gräfe, U. J. Antibiotics 2003, 56, 917.
4. (b) Kichiyama, T.; Yamada, Y. Patent application., JP 1997-161087, 1997, Chem. Abstr. 1997, 130, 153474.
5. Chaussard, J.; Folest, J. C.; Nédélec, J.-Y.; Périchon, J.; Sibille, S.; Troupel, M. Synthesis 1990, 369.
6. (a) Durandetti, M.; Sibille, S.; Nédélec, J.-Y.; Périchon, J. Synth. Commun. 1994, 2, 145.
7. (b) Durandetti, M.; Nédélec, J.-Y.; Périchon, J. J. Org. Chem. 1996, 61, 1748.
8. Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852.
9. Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1994, 50, 3529.
10. (a) Bakshi, S. P.; Turner, E. E. J. Chem. Soc. 1961, 171.
11. (b) Sock, O.; Troupel, M.; Périchon, J. Tetrahedron Lett. 1985, 26, 1509.
12. (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833.
13. (b) Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1979, 177, 273.
14. (c) Klingstedt, T.; Frejd, T. Organometallics 1983, 2, 598.
15. Rieu, J. P.; Boucherle, A.; Gousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095.
16. Shen, T. Y. Angew. Chem., Int. Ed. Engl. 1972, 11, 460.
17. (a) Durandetti, M.; Lachaise, I.; Nédélec, J.-Y.; Périchon, J. Patent application, FR 1997-7908, 1997, Chem. Abstr. 1997, 130, 188492.
18. (b) Durandetti, M.; Lachaise, I.; Nédélec, J.-Y.; Périchon, J. Patent application, WO 1998-FR1336, 1998, Chem. Abstr. 1998, 130, 188492.
19. (c) Durandetti, M.; Périchon, J.; Nédélec, J.-Y. J. Org. Chem. 1997, 62, 7914.
20. (a) Close, W. J. J. Org. Chem. 1950, 15, 1131.
21. (b) Roder, H.; Helmchen, G.; Peters, E. M.; Peters, K.; von Schnering, H.-G. Angew. Chem., Int. Ed. Engl. 1984, 23, 898.
22. Wenkert, E.; Fernandes, J. B.; Michelotti, E. L.; Swindell, C. S. Synthesis 1983, 701.
23. Kharash, M. S.; Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Coustable: London, 1954.
24. (a) Bumagin, N. A.; Kasatkin, A.; Beletskaya, I. P. Bull. Acad. Sci. USSR 1984, 33, 1696.
25. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995, 290.
26. Suzuki, S.; Shiono, M.; Fujita, Y. Synthesis 1983, 804.
27. (a) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
28. (b) Dübner, F.; Knöchel, P. Angew. Chem. Int. Ed. 1999, 38, 379.
29. (a) Gomes, P.; Gosmini, C.; Périchon, J. Patent application, FR 2001-08808, 2001, Chem. Abstr. 2001, 138, 79947.
30. (b) Gomes, P.; Gosmini, C.; Périchon, J. J. Org. Chem. 2003, 68, 1142.
31. (a) Schulz, E.; Fahmi, K.; Lemaire, M. Acros Org. Acta 1995, 1, 10.
32. (b) Roncali, J. Chem. Rev. 1997, 97, 173.
33. Gronowitz, S. Ark. Kemi 1958, 12, 533.
34. Durandetti, M.; Périchon, J.; Nédélec, J.-Y. Tetrahedron Lett. 1997, 38, 8683.
35. Mellah, M.; Labbé, E.; Nédélec, J.-Y.; Périchon, J. New J. Chem. 2002, 26, 207.
36. Cannes, C.; Condon, S.; Durandetti, M.; Périchon, J.; Nédélec, J.-Y. J. Org. Chem. 2000, 65, 4575.
37. Salamonczyk, G. M.; Han, K.; Guo, Z.-W.; Sih, C. J. J. Org. Chem. 1996, 61, 6893.
38. (a) Iseki, Y.; Watanabe, E.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1993, 115, 7313.
39. (b) Angeloni, L.; Castellucci, E.; Bartocci, G.; Mazzucato, U.; Spalletti; A.; Marconi, G. Gazz. Chim. Ital. 1996, 126, 609.
40. (c) Chen, C.-C.; Pan, K.; Wang, S.-L.; Ho, T.-I. J. Lumin. 1997, 71, 321.