Magnesium in water: simple and effective for pinacol-coupling

Abstract

References

1. For recent reviews on pinacol-coupling, see: T. Wirth, Angew. Chem., Int. Ed. Engl., 1996, 35, 61; G. M. Robertson, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, New York, 1991, vol. 3, ch. 2.6.
2. S. F. Nelsen and D. C. Kapp, J. Am. Chem. Soc., 1986, 108, 1265.
3. S. K. Pradhan and K. R. Thakker, Tetrahedron Lett., 1987, 28, 1813.
4. M. Gomberg and W. E. Bachmann, J. Am. Chem. Soc., 1927, 49, 236.
5. A. Fürstner, R. Csuk, C. Rohrer and H. Weidmann, J. Chem. Soc., Perkin Trans. 1, 1988, 1729.
6. J. B. Conant and H. B. Cutter, J. Am. Chem. Soc., 1926, 48, 1016.
7. J. L. Namy, J. Souppe and H. B. Kagan, Tetrahedron Lett., 1983, 24, 765.
8. T. Imamoto, T. Kusumoto, Y. Hatanaka and M. Yokoyama, Tetrahedron Lett., 1982, 23, 1353.
9. Z. Hou, K. Takamine, Y. Fujiwara and H. Taniguchi, Chem. Lett., 1987, 2061.
10. D. S. Hays and G. C. Fu, J. Am. Chem. Soc., 1995, 117, 7283.
11. M. Hulce and T. LaVaute, Tetrahedron Lett., 1988, 29, 525.
12. For reviews, see: A. Fürstner and B. Bogdanovi'c, Angew. Chem., Int. Ed. Engl., 1996, 35, 2443; J. E. McMurry, Chem. Rev., 1989, 89, 1513; B. E. Kahn and R. D. Rieke, Chem. Rev., 1988, 88, 733.
13. A. Clerici and O. Porta, Tetrahedron Lett., 1982, 23, 3517; A. Clerici and O. Porta, J. Org. Chem., 1982, 47, 2852; A. Gansauer, Chem. Commun., 1997, 457; A. Clerici, O. Porta and M. Riva, Tetrahedron Lett., 1981, 22, 1043 and refs cited therein M. C. Barden and J. Schwartz, J. Am. Chem. Soc., 1996, 118, 5484.
14. P. Delair and J. L. Luche, J. Chem. Soc., Chem. Commun., 1989, 398 See also, T. Tsukinoki, T. Kawaji, I. Hashimoto, S. Mataka and M. Tashiro, Chem. Lett., 1997, 235; K. Tanaka, S. Kishigmi and F. Toda, J. Org. Chem., 1990, 55, 2981.
15. H. J. Lim, G. Keum, S. B. Kang, B. Y. Chung and Y. Kim, Tetrahedron Lett., 1998, 39, 4367.
16. C. J. Li, Y. Meng, X. H. Yi, J. H. Ma and T. H. Chan, J. Org. Chem., 1997, 62, 8632.
17. 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; C. J. Li and T. H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997.