Rates and Mechanism of Biphenyl Synthesis Catalyzed by Electrogenerated Coordinatively Unsaturated Nickel Complexes

Organometallics

Volumn 7, Issue 10, 1988, Pages 2203-2214

  Amatore, Christian ^a   Jutand, Annv ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001724313     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00100a019     Document Type: Article

References (32)

1. (a) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D. J. Am. Chem. Soc. 1971, 93, 5908. (b) Semmelhack, M. F.; Ryono, L. S. J. Am. Chem. Soc. 1975, 97, 3873. (c) Semmelhack, M. F.; Helquist, P. M.; Jones, L. D.; Keller, L.; Mendelson, L.; Ryono, L. S.; Smith, J. G.; Stauffer, R. D. J. Am. Chem. Soc. 1981, 103, 6460.
2. See, e.g.: (a) Fanta, P. E. Chem. Rev. 1946, 38, 139. (b) Chem. Rev. 1964, 64, 613. (c) Fanta, P. E. Synthesis 1974, 9. (d) Cornforth, J.; Sierakowski, A. F.; Wallace, T. W. J. Chem. Soc., Chem. Commun. 1979, 294. (e) Rieke, R. D.; Rhyne, L. D. J. Org. Chem. 1979, 44, 3445. (f) Wittek, P. J.; Liao, J. K.; Cheng, C. C. J. Org. Chem. 1979, 44, 870.
3. Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 3375.
4. Zembayashi, M.; Tamao, K.; Yoshida, J.; Kumada, M. Tetrahedron Lett. 1977, 4089.
5. Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627.
6. (a) Troupel, M.; Rollin, Y.; Perichon, J.; Fauvarque, J. F. Nouv. J. Chim. 1981, 5, 621. (b) Fauvarque, J. F.; Chevrot, C.; Jutand, A.; Francois, M.; Perichon, J. J. Organomet. Chem. 1984, 264, 273.
7. (a) Troupel, M.; Rollin, Y.; Sibille, S.; Fauvarque, J. F.; Perichon, J. J. Chem. Res. Synop. 1980, 26. (b) Schiavon, G.; Bontempelli, G.; Corain, B. J. Chem. Soc., Dalton Trans. 1981, 1074.
8. Fauvarque, J. F.; Petit, M. A.; Pflüger, F.; Jutand, A.; Chevrot, C.; Troupel, M. Makromol. Chem., Rapid Commun. 1983, 4, 455.
9. (a) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360. (b) Hidai, M.; Kashiwagi, T.; Ikenchi, T.; Uchida, Y. J. Organomet. Chem. 1971, 30, 279. (c) Fahey, D. R. J. Am. Chem. Soc. 1970, 92, 402. (d) Fahey, D. R. Organomet. Chem. Rev., Sect. A 1972, 7, 245. (e) Fahey, D. R.; Mahan, J. D. J. Am. Chem. Soc. 1977, 99, 2501.
10. (a) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (b) J. Am. Chem. Soc. 1979, 101, 7547. (c) J. Org. Chem. 1980, 45, 1930.
11. See, e.g., ref 5, pp 2632–2633, or ref 10b, pp 7552–7554, for detailed presentations of the main mechanistic sequences proposed in the literature.
12. Matsumoto, H.; Inaha, S.-I.; Rieke, R. D. J. Org. Chem. 1983, 48, 840.
13. (a) Reference 10a, p 6322. (b) Troupel, M.; Rollin, Y.; Sibille, S.; Fauvarque, J. F.; Perichon, J. J. Chem. Res., Synop. 1980, 24.
14. Fauvarque, J. F.; Pflüger, F. J. Organomet. Chem. 1981, 208, 419.
15. (a) Sock, O.; Troupel, M.; Perichon, J.; Chevrot, C.; Jutand, A. J. Electroanal. Chem. 1985, 183, 237.
16. Amatore, C. A.; Jutand, A.; Pflüger, F. J. Electroanal. Chem. 1987, 218, 361.
17. (a) Amatore, C.; Gareil, M.; Savéant, J.-M. J. Electroanal. Chem. 1983, 147, 1. (b) Amatore, C.; Savéant, J.-M. J. Electroanal. Chem. 1983, 144, 59. (a) Bard, A. J.; Faulkner, L. R. In Electroanalytical Methods; Wiley: New York, 1980. (b) Andrieux, C. P.; Savéant, J. M. In Investigation of Rates and Mechanism of Reactions; Bernasconi, C. F., Ed.; Wiley: New York, 1986; Vol. 6, 4/E, Part 2, pp 305–390.
18. (a) See, e.g.: Corain, B.; Bressan, M.; Rigo, P.; Turco, A. Chem. Commun. 1968, 509. Aresta, M.; Nobile, C. F.; Sacco, A. Inorg. Chim. Acta 1975, 12, 167, for analogue dimeric nickel(I) species. (b) Vide infra and footnote 33 for the determination of the rate constant of nickel(I) dimerization. (c) The concentration dependence in Figure 3b (note the C° factor on the lower and upper scales) excludes any pseudo-first-order pathway in the Ni(I) chemical fate; see, e.g.: Amatore, C.; Garreau, D.; Hammi, M.; Pinson, J.; Savéant, J.-M, J. Electroanal. Chem. 1985, 184, 1 and ref 20.
19. Bard, A. J.; Kojima, H. J. Am. Chem. Soc. 1975, 97, 6317.
20. (a) Fauvarque, J. F.; Jutand, A. Bull. Soc. Chim. Fr. 1976, 765. (b) Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1979, 177, 273.
21. 2(dppe): Coronas, J. M.; Rossell, O.; Sales, J. J. Organomet. Chem. 1975, 97, 473.
22. See, e.g.; (a) Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706. (b) Andrieux, C. P.; Blocman, C,; Dumas-Bouchiat, J.-M., M'Halla, F.; Savéant, J. M. J. Am. Chem. Soc. 1980, 102, 3806 and references therein. (c) Hershberger, J. W.; Amatore, C.; Kochi, J. K. J. Organomet. Chem. 1983, 250, 345. (29) Compare ref 5, p 2630.
23. Almemark, M.; Akermark, B. J. Chem. Soc., Chem. Commun. 1978, 66.
24. (a) Morrell, D. G.; Kochi, J. K. J. Am. Chem. Soc. 1975, 97, 7262. (b) With triethylphosphine electrochemical oxidation of the arylnickel(I) halide affords excellent yields of arylphosphonium salt: Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1978, 100, 1634.
25. For stable arylnickel(III) complexes see, e.g.: (a) Grove, D. M.; van Koten, G.; Zoet, R. J. Am. Chem. Soc. 1983, 105, 1379. (b) Grove, D. M.; van Koten, G.; Mul, W. P.; van der Zeijden, A. A. H.; Terheijden, J.; Zoutberg, M. C.; Stam, C. H. Organometallics 1986, 5, 322.
26. Amatore, C.; Saveant, J.-M. J. Electroanal. Chem. 1981, 123, 189.
27. 2(dppe).
28. Amatore, C.; Mottier, L.; Jutand, A., manuscript in preparation.
29. Howell, J. O.; Kuhr, W. G.; Ensman, R. E.; Wightman, R. M. J. Electroanal. Chem. 1986, 209, 77.
30. Casabo, J.; Coronas, J. M.; Sales, J. Inorg. Chim. Acta 1974, 11, 5.
31. Heineman, W. R.; Kissinger, P. T. In Laboratory techniques in Electroanalytical Chemistry; Kissinger, P. T., Heineman, W. R., Eds.; Marcel Dekker: New York and Basel, 1984; p 115.
32. Zara, A. J.; Machado, S. S.; Bulhoes, L. O. S.; Benedetti, A. V.; Rabockai, T. J. Electroanal. Chem. 1987, 221, 165.