Aluminium-mediated Reductive Dimerization of Aromatic Dialdehydes

Abstract

Pinacol coupling reaction of several aromatic dialdehydes 1a–d using inexpensive aluminum powder as a reductive reagent in aqueous NaOH–methanol media afforded dimeric compounds 2a–d as main products, in which only one carbonyl group of 1 was reduced.

References

1. See, for example: J. Souppe, L. Danon, J. L. Namy and H. B. Kagan, J. Organomet. Chem., 1983, 250, 227; J. M. Khurana and A. Sehgal, J. Chem. Soc., Chem. Commun., 1994, 571; T. Tsukinoki, T. Kawaji, I. Hashimoto, S. Mataka and M. Tashiro, Chem. Lett., 1997, 235; J. Grimshaw and J. S. Ramsey, J. Chem. Soc. C, 1966, 653.
2. T. Tsukinoki, T. Kawaji, I. Hashimoto, T. Etoh, D. A. Sahade and M. Tashiro, Eng. Sci. Reports, Kyushu University, 1997, 19, 15.
3. Z. Hu, C. Scordilis-Kelley and M. P. Cava, Tetrahedron Lett., 1993, 34, 1879.
4. D. A. Sahado, S. Mataka, T. Sawada, T. Tsukinoki and M. Tashiro, Tetrahedron Lett., 1997, 38, 3745; D. Tanner and O. Wennerström, Tetrahedron Lett., 1981, 22, 2313.
5. A. Wayne Cooke and K. B. Wagener, Macromolecules, 1991, 24, 1404.
6. J. H. Stocker, D. H. Kern and R. M. Jenevein, J. Org. Chem., 1968, 33, 412.
7. A. Clerici and O. Porta, Tetrahedron Lett., 1982, 23, 3517.
8. J. H. Wood, C. C. Tung, M. A. Perry and R. E. Gibson, J. Am. Chem. Soc., 1950, 72, 2992.
9. K. Bowden, A. M. Butt and M. Streater, J. Chem. Soc., Perkin Trans. 2, 1992, 567.
10. A. A. Baum, J. Am. Chem. Soc., 1972, 94, 6866; C. C. Leznoff and Y. Wong, Can. J. Chem., 1973, 51, 3756.
11. M. Tashiro and T. Yamato, J. Org. Chem., 1981, 46, 1543.