Cathodic carbonylation. Synthesis of aliphatic aldehydes using an electroreductively generated iron-carbonyl anion

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 15, 1996, Pages 1873-1877

  Yoshida, Kunihisa ^a   Kuwata, Hideki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749088911     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001873     Document Type: Article

References (57)

1. (a) J. P. Collman, R. G. Finke, J. N. Cawse and J. I. Brauman, J. Am. Chem. Soc., 1977, 99, 2515;
2. (b) J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1987.
3. (a) M. P. Cooke, Jr., J. Am. Chem. Soc., 1970, 92, 6080;
4. (b) J. P. Collman, S. R. Winter and D. R. Clark, J. Am. Chem. Soc., 1972, 94, 1788;
5. (c) J. P. Collman, S. R. Winter and R. G. Komoto, J. Am. Chem. Soc., 1973, 95, 249;
6. (d) J. P. Collman, Acc. Chem. Res., 1975, 8, 342;
7. (e) R. D. Pike, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, Chichester, 1995, vol. 4, p. 2299.
8. R. F. Heck, in Organic Syntheses via Metal Carbonyls, vol. 1, eds. I. Wender and P. Pino, Wiley-Interscience, New York, 1968, pp. 373-403;
9. R. F. Heck, in Advances in Catalysis, vol. 26, eds. D. D. Eley, H. Pines and P. B. Weisz, Academic, New York, 1977, pp. 323-349;
10. T. A. Weil, L. Cassar and M. Foa, in Organic Syntheses via Metal Carbonyls, vol. 2, eds. I. Wender and P. Pino, Wiley-Interscience, New York, 1977, pp. 517-543;
11. H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Plenum, New York, 1991.
12. (a) H. Alper, Adv. Organomet. Chem., 1981, 19, 183;
13. (b) H. des Abbayes, Isr. J. Chem., 1985, 26, 249;
14. (c) W. J. Kerr, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, Chichester, 1995, vol. 7, p. 4633.
15. (a) M. Ryang, Organomet. Chem. Rev. A, 1970, 5, 67;
16. (b) W. O. Siegl and J. P. Collman, J. Am. Chem. Soc., 1972, 94, 2516;
17. (c) M. Yamashita, K. Miyoshi, Y. Nakazono and R. Suemitsu, Bull. Chem. Soc. Jpn., 1982, 55, 1663.
18. K. Yoshida, E. Kunugita, M. Kobayashi and S. Amano, Tetrahedron Lett., 1989, 30, 6371.
19. K. Yoshida, M. Kobayashi and S. Amano, J. Chem. Soc., Perkin Trans. 1, 1992, 1127.
20. C. Amatore, P. J. Krusic, S. U. Pedersen and J.-N. Verpeaux, Organometallics, 1995, 14, 640.
21. G. Tanguy, B. Weinberger and H. des Abbayes, Tetrahedron Lett., 1984, 25, 5529;
22. H. des Abbayes, J.-C. Clement, P. Laurent, G. Tanguy and N. Thilmont, Organometallics, 1988, 7, 2293;
23. Y. Kimura, Y. Tomita, S. Nakanishi and Y. Otsuji, Chem. Lett., 1979, 321.
24. I. Rhee, M. Ryang and S. Tsutsumi, J. Organomet. Chem., 1967, 9, 361.
25. (a) J. K. Kotz, in Topics in Organic Electrochemistry, eds. A. J. Fry and W. E. Britton, Plenum, New York, 1986, p. 119;
26. (b) C. Amatore, J.-N. Verpeaux and P. J. Krusic, Organometallics, 1988, 7, 2426;
27. (c) Y. Zhen and J. D. Atwood, Organometallics, 1991, 10, 2778;
28. (d) D. J. Curran, P. B. Graham and M. D. Rausch, Organometallics, 1993, 12, 2380.
29. M. D. Hawley, in Encyclopedia of Electrochemistry of the Elements, Organic Section vol. XIV, eds. A. J. Bard and H. Lund, Dekker, New York, 1980, ch. XIV-1;
30. J. Y. Becker, in The Chemistry of Functional Groups, Supplement D, eds. S. Patai and Z. Rappoport, Wiley-Interscience, Chichester, 1983, ch. 6;
31. A. J. Fry, Synthetic Organic Electrochemistry, 2nd edn., Wiley-Interscience, New York, 1989, ch. 5;
32. D. G. Peters, in Organic Electrochemistry, 3rd edn., eds. H. Lund and M. M. Baizer, Dekker, New York, 1991, ch. 8.
33. (a) B. M. Peake, B. H. Robinson, J. Simpson and D. J. Watson, J. Chem. Soc., Chem. Commun., 1974, 945;
34. (b) S. A. Fairhurst, J. R. Morton and K. F. Preston, J. Chem. Phys., 1982, 77, 5872;
35. (c) B. M. Peake, M. C. R. Symons and J. L. Wyatt, J. Chem. Soc., Dalton Trans., 1983, 1171.
36. A. B. Anderson and D. B. Kang, Inorg. Chem., 1984, 23 1170.
37. B. A. Narayanan and J. K. Kochi, J. Organomet. Chem., 1984, 272, C49;
38. B. A. Narayanan, C. Amatore and J. K. Kochi, Organometallics, 1986, 5, 926.
39. J. K. Burdett, J. Chem. Soc., Chem. Commun., 1973, 763;
40. J. K. Burdett, Coord. Chem. Rev., 1978, 27, 1;
41. R. C. Dunbar and B. B. Hutchinson, J. Am. Chem. Soc., 1974, 96, 3816;
42. J. H. Richardson, L. M. Stephenson and J. I. Brauman, J. Am. Chem. Soc., 1974, 96, 3671;
43. M. S. Foster and J. L. Beauchamp, J. Am. Chem. Soc., 1975, 97, 4808.
44. P. J. Krusic, J. S. Filippo, Jr., B. Hutchinson, R. L. Hance and L. M. Daniels, J. Am. Chem. Soc., 1981, 103, 2129.
45. P. C. Engelking and W. C. Lineberger, J. Am. Chem. Soc., 1979, 101, 5569.
46. M. T. Jones, R. N. McDonald, P. L. Schell and M. H. Ali, J. Am. Chem. Soc., 1989, 111, 5983.
47. T. H. Morton, Tetrahedron, 1982, 38, 3195.
48. J. F. Garst, Acc. Chem. Res., 1971, 4, 400;
49. Y. Huang and D. D. M. Wayner, J. Am. Chem. Soc., 1994, 116, 2157.
50. P. J. Krusic, W. J. Cote and A. Grand, J. Am. Chem. Soc., 1984, 106, 4642.
51. P. Laurent, G. Tanguy and H. des Abbayes, J. Chem. Soc., Chem. Commun., 1986, 1754.
52. D. Vanhoye, F. Bedioui, A. Mortreux and F. Petit, Tetrahedron Lett., 1988, 29, 6441.
53. See e.g. K. Yoshida, Electrooxidation in Organic Chemistry, Wiley-Interscience, New York, 1984; Krieger, Malabar, Florida, 1993.
54. Reference 25, p. 27.
55. K. Maruyama, M. Taniuchi and S. Oka, Bull. Chem. Soc. Jpn., 1974, 47, 712;
56. B. Bachman, Org. Synth., Coll. Vol. II, p. 323.
57. C. K. Mann, in Electroanalytical Chemistry, ed. A. J. Bard, Dekker, New York, 1969, vol. 3, p. 57.