Reductive Coupling of Aromatic Carbonyl Compounds to Pinacols Using Zinc Powder in Aqueous Media†

Abstract

Zinc-mediated reductive coupling of aromatic carbonyl compounds occurs to give corresponding 1,2-diols in moderate to good yields in saturated NH₄Cl(aq)–THF solution at room temperature.

References

1. A. Ghribi, A. Alexakis and J. F. Normant, Tetrahedron Lett., 1984, 3083.
2. B. E. Kahn and E. D. Rieke, Chem. Rev., 1988, 88, 733; J. M. Pons and M. Santelli, Tetrahedron, 1988, 44, 4295.
3. A. Clerici and O. Porta, Tetrahedron Lett., 1982, 23, 3517.
4. K. Tanaka, S. Kishigami and F. Toda, J. Org. Chem., 1990, 55, 2981.
5. M. Hulce and T. LaVaute, Tetrahedron Lett., 1988, 29, 525.
6. M. C. Barden and J. Schwartz, J. Am. Chem. Soc., 1996, 118, 5484.
7. C. J. Li, Y. Meng, X. H. Yi, J. Ma and T. H. Chan, J. Org. Chem., 1997, 62, 8632.
8. C. J. Li, Chem. Rev., 1993, 93, 2023; A. Lubineau, J. Auge and Y. Queneau, Synthesis, 1994, 741; C. J. Li, Tetrahedron, 1996, 52, 5643.
9. C. Petrier and J. L. Luche, J. Org. Chem., 1985, 50, 910; J. Einhorn and J. L. Luche, J. Organomet. Chem., 1987, 322, 177; S. R. Wilson and M. E. Guazzaroni, J. Org. Chem., 1989, 54, 3087.
10. Y. Handa and J. Inanaga, Tetrahedron Lett., 1987, 28, 5717; R. E. Balsells and A. R. Frasca, Tetrahedron, 1982, 38, 2525.