Aerobic catalytic oxidative coupling of 2-naphthols and phenols by VO(acac)₂

Abstract

In the presence of a catalytic amount of VO(acac)₂, oxidative coupling of 2-naphthol or phenol derivatives with molecular oxygen occurred at room temperature and selectively gave the corresponding ortho–ortho coupling products in moderate to high yields.

References

1. For recent reviews see: (a) C. Rosini, L. Franzini, A. Raffaelli and P. Salvadori, Synthesis, 1991, 503; (b) H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; (c) K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021; (d) L. Pu, Chem. Rev., 1998, 98, 2405.
2. (a) F. Toda, K. Tanaka and S. Iwata, J. Org. Chem., 1989, 54, 3007; (b) R. Pummerer, E. Prell and A. Rieche, Ber., 1926, 59, 2159; (c) B. Feringa and H. Wynberg, J. Org. Chem., 1981, 46, 2547.
3. M. J. S. Dewar and T. Nakaya, J. Am. Chem. Soc., 1968, 90, 7134; K. Yamamoto, H. Fukushima, Y. Okamoto, K. Hatada and M. Nakazaki, J. Chem. Soc., Chem. Commun., 1984, 1111.
4. (a) B. Feringa and H. Wynberg, Tetrahedron Lett., 1977, 18, 4447; (b) J. Brussee, J. L. G. Groenendijk, J. M. te Koppele and A. C. A. Jansen, Tetrahedron, 1985, 41, 3313; (c) M. Smrcina, J. Polakova, S. Vyskocil and P. Kocovsky, J. Org. Chem., 1993, 58, 4534.
5. M. Noji, M. Nakajima and K. Koga, Tetrahedron Lett., 1994, 35, 7983.
6. T. Sakamoto, H. Yonehara and C. Pac, J. Org. Chem., 1994, 59, 6859.
7. For a recent review see: T. Hirao, Chem. Rev., 1997, 97, 2707.
8. M. A. Schwartz, R. A. Holton and S. W. Scott, J. Am. Chem. Soc., 1969, 91, 2800; J. D. White, R. J. Butlin, H.-G. Hahn and T. Johnson, J. Am. Chem. Soc., 1990, 112, 8595; D. A. Evans, C. J. Dinsmore, D. A. Evrard and K. M. DeVries, J. Am. Chem. Soc., 1993, 115, 6426; D. L. Comins and L. A. Morgan, Tetrahedron Lett., 1991, 32, 5919; W. L. Carrick, G. L. Karapinka and G. T. Kwiatkowski, J. Org. Chem., 1969, 34, 2388.
9. M. K. O'Brien and B. Vanasse, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, vol. 8, pp. 5482–5485.
10. B. E. Rossiter, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, New York, 1995, vol. 8, pp. 5479–5482.
11. For 4a see: G. Sartori, R. Maggi, F. Bigi, A. Arienti, G. Casnati, G. Bocelli and G. Mori, Tetrahedron, 1992, 48, 9483 for 4b see: D. R. Armstrong, C. Cameron, D. C. Nonhebel and P. G. Perkins, J. Chem. Soc., Perkin Trans. 2, 1983, 581.