Electrosynthèses de composés carbonylés catalysées par des complexes du nickel : Activation du monoxyde de carbone ou de composés acylés

Canadian Journal of Chemical Engineering

Volumn 76, Issue 6, 1998, Pages 1013-1019

  Troupel, Michel ^a   Oçafrain, Maiténa ^a   Dolhem, Eric ^a   Folest, Jean Claude ^a   Barhdadi, Rachid ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039608292     PISSN: 00084034     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjce.5450760607     Document Type: Article

References (39)

1. 5 Revisited", J. Organometallics 7, 2426-2428 (1988).
2. Amatore, C., P. J. Krusic, S. U. Pedersen et J. N. Verpeaux, "Rate and Mechanism of the Reductions of Iron Pentacarbonyl and Chromium Hexacarbonyl to their Metalate Complexes", Organometallics 14, 640-649 (1995).
3. Amatore, C., E. Carré, A. Jutand, H. Tanaka, S. Torri, I. Chiarotto et I. Carelli, "Direct vs Indirect Route in the Activation of Aroylpalladium(II) Complexes by Electron Transfer", Electrochim. Acta 42, 2143-2152 (1997).
4. 4]", J. Organometal Chem. 486, 275-277 (1995).
5. Baillargeon, V. P. et J. K. Stille, "Palladium-Catalyzed Formylation of Organic Halides with Carbon Monoxide and Tin Hydride", J. Amer. Chem. Soc. 108, 452-461 (1986).
6. Brunet, J. J. et R. Chauvin, "Synthesis of Diarylketones Through Carbonylative Coupling", Chem. Soc. Rev. 24, 89-95 (1995).
7. Ben-David, Y., M. Portnoy et D. Milstein, "Formylation of Aryl Chlorides Catalyzed by a Palladium Complex", J. Chem. Soc., Chem. Comm. 1816-1817 (1989).
8. -3 mol/L", Inorg. Chem. 1, 30-36 (1962).
9. Chaussard, J., J. C. Folest, J. Y. Nédélec, J. Périchon, S. Sibille et M. Troupel, "Use of Sacrificial Anodes in Electrochemical Functionalization of Organic Balide", Synthesis 369-381 (1990).
10. 2 in the Presence of Carbon Monoxide and its Use in the Palladium-Catalyzed Electrochemical Formylation of Iodoanisole", Electrochim. Acta 41, 2503-2509 (1996).
11. Collman, J. P., "Disodium Tetracarbonylferrate - A Transition -Metal Analog of a Grignard Reagent", Acc. Chem. Res. 8, 342-347 (1975).
12. 4 Supernucleophile", J. Amer. Chem. Soc. 99, 2515-2526 (1977).
13. 4]- Alkyl Migration Reactions. A Mechanistic Investigation", J. Amer. Chem. Soc. 100, 4766-4772 (1978).
14. Colquhoun, H. M., D. J. Thompson et M. V. Twigg, "Carbonylation: Direct Synthesis of Carbonyl Compounds", Plenum Press, New York and London (1991).
15. Curran, D. J., P. B. Graham et M. D. Rausch, "Infrared Spectroelectrochemical Observation of the Reduction of Iron Pentacarbonyl", Organometallics 12, 2380-2382 (1993).
16. 2 to CO", J. Electroanal. Chem. 219, 259-271 (1987).
17. Dessy, R. E., P. M. Weissman et R. L. Pohl, "Organometallic Electrochemistry. VI. Electrochemical Scission of Metal -Metal Bonds", J. Amer. Chem. Soc. 88, 5117-5121 (1966).
18. Dolhem, E., M. Oçafrain, J. Y. Nédélec et M. Troupel, "Nickel Catalyzed Electrosynthesis of Ketones from Organic Halides and Metal Carbonyls, Tetrahedron 53, 17089-17096 (1997).
19. Folest, J. C., E. Pereira-Martins, M. Troupel et J. Périchon, "Electrochemical Synthesis of Symmetrical Ketones from Acid Chlorides", Tetrahedron Letters 34, 7571-7574 (1993).
20. Garnier, L. Y. Rollin et J. Périchon, "Electrosynthesis of Symmetrical Ketones from Organic Halides and Carbon Dioxide Catalyzed by 2,2′ Bipyridine - Nickel Complexes", J. Organomet. Chem. 367, 347-358 (1989).
21. 2 en CO", Nouv. J. Chim. 13, 53-59 (1989).
22. Marzouk, H., Y. Rollin, J. C. Folest, J. Y. Nédélec et J. Périchon, "Electrochemical Synthesis of Ketones from Acid Chlorides and Alkyl and Aryl Halides Catalyzed by Nickel Complexes", J. Organomet. Chem. 369, C47-C50 (1989).
23. Nyholm, R. S. et L. N. Short, "The Structure of Nickel Tetracarbonyl and some Disubstuted Derivatives", J. Chem. Soc. 2670-2673 (1953).
24. Oçafrain, M., M. Devaud, M. Troupel et J. Périchon, "New Electrochemical Synthesis of Ketones from Organic Halides and Carbon Monoxide", J. Chem. Soc., Chem. Commun. 2331-2332 (1995).
25. Oçafrain, M. M. Devaud, J. Y. Nédélec et M. Troupel, "Electrochemical Generation of a Nickel-Carbonyl Complex, Catalyst for the Electroreductive Coupling of Organic Balides and Monoxide into Ketones", J. Organomet. Chem. 560, 103-107, (1998).
26. Pickett, C. J. et D. Pletcher, "Electrochemical Oxidation and Reduction of Binary Metal Carbonyls in Aprotic Solvents", J. Chem. Soc., Dalton Trans. 879-386 (1975).
27. Rhee, I., N. Mizuta, M. Ryang et S. Tsutsumi, "The Benzylation and Phenylation Reactions of Unsaturated Compounds using Organo Monohalides and Polynuclear Iron Carbonyl", Bull. Chem. Soc. Jpn. 41, 1417-1422 (1968).
28. Rhee, I., M. Ryang, S. Murai et N. Sonoda, "The Reaction of Organic Halides with Cobalt Carbonyl", Chem. Lett. 909-910 (1978).
29. Rollin, Y. M., Troupel, D. G. Tuck et J. Périchon, "The Coupling of Organic Groups by the Electrochemical Reduction of Organic Halides: Catalysis by 2,2′ Bipyridinenickel Complexes", J. Organomet. Chem. 303, 131-137 (1986).
30. Schoenberg, A. et Heck, R. F., "Palladium Catalyzed Formylation of Aryl, Heterocyclic and Vinylic Halides", J. Amer. Chem. Soc. 96, 7761-7764 (1974).
31. Seurat, A., P. Lemoine et M. Gross, "Electrochemical Behaviour of Carbonyl Derivatives of Cr. Mo, W", Electrochim. Acta 23, 1219-1225.
32. Seyferth, D. et R. J. Spohn, "A Novel Mercurial - Based Symmetrical Ketone Synthesis", J. Amer. Chem. Soc. 91, 3037-3044 (1969).
33. Tamaru, Y., H. Ochiai, Y. Yamada et Z. I. Yoshida, "Unsymmetrical Ketone Synthesis via Palladium Catalyzed Carbonylation of Organic Halides", Tetrahedron Lett. 24(36), 3869-3872 (1983).
34. Troupel, M., Y. Rollin, O. Sock, G. Meyer et J. Périchon, "Electrochimie de complexes du nickel associé à la 2,2′ bipyridine dans le solvant N-méthylpyrrolidone. Application à l'activation de liaisons carbonehalogène", Nouv. J. Chim. 10, 593-599 (1986).
35. Uhlig, E. et D. Walther, "Synthesis with Electron-Rich Triad Complexes", Coord. Chem. Rev. 33, 3-53 (1980).
36. 5", Tetrahedron Lett. 29(49), 6441-6442 (1988).
37. Yoshida, K., E. I. Kunugita, M. Kobayashi et S. I. Amano, "Electrochemical Preparation and Reactions of Unmasked Acyl - Anion Synthons", Tetrahedron Lett. 30(46), 6371-6374 (1989).
38. Yoshida, K., M. Kobayashi et S. I. Amano, "Cathodic Carbonylation of 1-Halogenopentanes", J. Chem. Soc. Perkin Trans. 1, 1127-1129 (1992).
39. Yoshida, K. et H. Kuwata, "Cathodic Carbonylation. Synthesis of Aliphatic Aldehydes using an Electroreductively Generated Iron - Carbonyl Anion", J. Chem. Soc. Perkin Trans. 1, 1873-1877 (1996).