Novel one-pot vicinal double C-acylation of styrenes and methacrylates by electroreduction

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2755-2758

  Yamamoto, Yoshimasa ^a   Maekawa, Hirofumi ^a   Goda, Satoshi ^a   Nishiguchi, Ikuzo ^a  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CARBOXYLIC ACID; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; METHACRYLIC ACID DERIVATIVE; STYRENE DERIVATIVE; ZINC;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ELECTRODE; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0141631475     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035020v     Document Type: Article

References (28)

1. (a) Wenkert, E. Acc. Chem. Res. 1980, 13, 27.
2. (b) McMurry, J. E.; Melton, J. J. Am. Chem. Soc. 1971, 93, 5309.
3. (c) Miyashita, M.; Yanami, T.; Yoshikoshi, A. J. Am. Chem. Soc. 1976, 98, 4679.
4. (d) Mukaiyama, T.; Narasaka, K.; Furusato, M. J. Am. Chem. Soc. 1972, 94, 8641.
5. (e) Herrmann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 14, 3275.
6. (a) Nienhouse, E. J.; Irwin, R. M.; Finni, G. R. J. Am. Chem. Soc. 1967, 89, 4557.
7. (b) Adams, R.; Gold, M. H. J. Am. Chem. Soc. 1940, 62, 56.
8. (c) Lauer, W.; Spielman, M. A. J. Am. Chem. Soc. 1933, 55, 4923.
9. (d) Nowlin, G. J. Am. Chem. Soc. 1950, 72, 5754.
10. (e) Lutz, R. E.; Wilder, F. N. J. Am. Chem. Soc. 1934, 56, 1987.
11. (f) Gaertner, R.; Tonkyn, R. G. J. Am. Chem. Soc. 1951, 73, 5872.
12. (g) Jones, R. G. J. Am. Chem. Soc. 1955, 77, 4069.
13. (a) Jones, R. G. J. Am. Chem. Soc. 1955, 77, 4069.
14. (b) Young, D. M.; Allen, C. F. H. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p 219.
15. (a) Gaertner, R.; Tonkyn, R. G. J. Am. Chem. Soc. 1951, 73, 5872.
16. (b) Jones, R. G. J. Am. Chem. Soc. 1955, 77, 4069.
17. (c) Wolf, D. E.; Folkers, K. Org. React. 1951, 6, 410.
18. (d) Youtz, M. A.; Perkins, P. P. J. Am. Chem. Soc. 1929, 51, 3511.
19. (a) Shono, T.; Nishiguchi, I.; Ohmizu, H. J. Am. Chem. Soc. 1977, 99, 7396.
20. (b) Ohno, T.; Aramaki, H.; Nakahiro, H.; Nishiguchi, I. Tetrahedron 1996, 52, 1943.
21. (c) Ohno, T.; Sakai, M.; Ishino, Y.; Shibata, T.; Maekawa, H.; Nishiguchi, I. Org. Lett. 2001, 3, 3439.
22. (d) Nishiguchi, I.; Yamamoto, Y.; Sakai, M.; Ohno, T.; Ishino, Y.; Maekawa, H. Synlett 2002, 759.
23. Senboku, H.; Komatsu, H.; Fujimura, Y.; Tokuda, M. Synlett 2001, 418.
24. In the electroreductive vicinal double C-formylation of styrene, the double C-formylated products were not isolated, but were characterized as the corresponding O-methyloxime derivatives. See: Engels, Y.; Schäfer, H. J. Angew. Chem., Int. Ed. Engl. 1978, 17, 460.
25. Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 1, 351.
26. The styrenes, 1d-f,h, were prepared by Wittig reaction, and 1b and 1c were prepared by the reported method. See: Ishino, Y.; Mihara, M.; Nishihama, S.; Nishiguchi, I. Bull. Chem. Soc. Jpn. 1998, 71, 2669.
27. 4 by filtration and evaporation of the solvent, the isolation by column chromatography gave diacylated compounds in satisfactory yields.
28. This hypothesis is consistent with the phenomenon obtained in Mg-promoted silylation of aromatic active olefins. Simply hydrogenated products are easier to form than the corresponding silylated products in the reaction of the starting substrates possessing less negative reduction potentials, giving more stable anion species through electron transfer from Mg-metal. See: Kyoda, M.; Yokoyama, T.; Kuwahara, T.; Maekawa, H.; Nishiguchi, I. Chem. Lett. 2002, 228.