Electrochemical carboxylation of aliphatic ketones: Synthesis of β-keto carboxylic acids

Electrochemistry

Volumn 74, Issue 8, 2006, Pages 612-614

  Senboku, Hisanori ^a   Yamauchi, Yusuke ^a   Fukuhara, Tsuyoshi ^a   Hara, Shoji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Electrochemical Carboxylation; Fixation of Carbon Dioxide; Reactive Metal Anode; Keto Carboxylic Acids

Indexed keywords

ANODES; ATMOSPHERIC PRESSURE; CARBON DIOXIDE; CARBOXYLIC ACIDS; CATHODES; ELECTROCHEMISTRY; MAGNESIUM PRINTING PLATES; PLATINUM;

ALIPHATIC KETONES; CH3; ELECTROCHEMICAL CARBOXYLATION; REACTIVE METAL ANODES;

KETONES;

EID: 33749004502     PISSN: 13443542     EISSN: None     Source Type: Journal    
DOI: 10.5796/electrochemistry.74.612     Document Type: Article

References (32)

1. a) G. Silvestri, S. Gambino, G. Filardo, and A. Gulotta, Angew. Chem. Int. Ed. Engl., 23, 979 (1984).
2. b) G. Silvestri, S. Gambino, and G. Filardo, Acta Chem. Scand., 45, 987 (1991).
3. a) O. Sock, M. Troupel, and J. Périchon, Tetrahedron Lett., 26, 1509 (1985).
4. b) J. Chaussard, J. C. Folest, J. Y. Nédélec, J. Périchon, S. Sibille, and M. Troupel, Synthesis, 1990, 369.
5. H. Kamekawa, H. Senboku, and M. Tokuda, Electrochim. Acta, 42, 2117 (1997).
6. H. Kamekawa, H. Kudo, H. Senboku, and M. Tokuda, Chem. Lett., 1997, 917.
7. H. Kamekawa, H. Senboku, and M. Tokuda, Tetrahedron Lett., 39, 1591 (1998).
8. M. Tokuda, A. Yoshikawa, H. Suginome, and H. Senboku, Synthesis, 1997, 1143.
9. C. Kuang, Q. Yang, H. Senboku, and M. Tokuda, Chem. Lett., 34, 528 (2005).
10. H. Senboku, Y. Fujimura, H. Kamekawa, and M. Tokuda, Electrochim. Acta, 45, 2995 (2000).
11. H. Senboku, H. Kanaya, Y. Fujimura, and M. Tokuda, J. Electroanal Chem., 507, 82 (2001).
12. H. Senboku, H. Kanaya, and M. Tokuda, Synlett, 2002, 140.
13. H. Senboku, H. Komatsu, Y. Fujimura, and M. Tokuda, Synlett, 2001, 418.
14. M. A. Chowdhury, H. Senboku, and M. Tokuda, Tetrahedron, 60, 475 (2004).
15. G. Silvestri, S. Gambino, and G. Filardo, Tetrahedron Lett., 27, 3429 (1986).
16. S. Mcharek, M. Heintz, M. Troupel, and J. Périchon, Bull. Soc. Chem. Fr., 1989, 95.
17. a) Y. Ikeda and E. Manda, Chem. Lett., 1984, 453.
18. b) Y. Ikeda and E. Manda, Bull. Chem. Soc. Jpn., 58, 1723 (1985).
19. A. S. C. Chan, T. T. Huang, J. H. Wagenknecht, and R. E. Miller, J. Org. Chem., 60, 742 (1995).
20. a) J. Damodar, R. R. Raju, and S. J. Reddy, Ind. J. Chem., Sec. B, 41B, 2655 (2002).
21. b) J. Damodar, S. R. K. Mohan, and S. R. J. Reddy, Synthesis, 2002, 399.
22. H. Senboku and M. Tokuda, Fain Kemikaru, 31, 50 (2002) [in Japanese].
23. Analytical studies on iron- or ruthenium-catalyzed electrochemical carboxylation of cyclohexanone have been reported: a) K. Tanaka, H. Miyamoto, and T. Tanaka, Chem. Lett., 1988, 2033.
24. b) K. Tanaka, R. Wakita, and T. Tanaka, J. Am. Chem. Soc., 111, 2428 (1989).
25. 2 has been also reported: c) A. P. Doherty, Electrochim. Acta, 47, 2963 (2002).
26. -1 of electricity was effective for higher conversion of ketone 1, even though it was not sufficient yet for the consumption of I.
27. R. E. Tirpak, R. S. Olsen, and M. W. Rathke, J. Org. Chem., 50, 4877 (1985).
28. T. Sasaki, T. Katayama, and A. Takeda, J. Org. Chem., 46, 2924 (1981).
29. 3N gave β-keto carboxylic acid: a) N. Matsumura, T. Yagyu, and E. Imoto, Nippon Kagaku Kaishi, 1977, 1344 [in Japanese].
30. b) See ref. 20.
31. If the generation of enolate A would proceed only through deprotonation by anion radical of 1 resulting in the formation of hydromonomer and/or hydrodimer of ketone 1, the yield of carboxylic acid 2 should be theoretically less than 67% yield.
32. 2 has more positive reduction peak potential than that of la. See ref. 8 and 11.