Novel two-phase oxidative cross-coupling of the two-component molecular crystal of 2-naphthol and 2-naphthylamine

Abstract

Two-phase reaction of a two-component molecular crystal of 2-naphthol and 2-naphthylamine suspended in aqueous Fe³⁺ solutions gives a cross-coupling product, 2-amino-2′-hydroxy-1,1′-binaphthalene, with good selectivity.

References

1. F. Toda, Synlett, 1993, 303.
2. F. Toda, K. Tanaka and S. Iwata, J. Org. Chem., 1989, 54, 3007.
3. K. Ding, Y. Wang, L. Zhang, Y. Wu and T. Matsuura, Tetrahedron, 1996, 52, 1005.
4. E. Carreira, R. A. Singer and W. Lee, J. Am. Chem. Soc., 1994, 116, 8837; E. Carreira, W. Lee and R. A. Singer, J. Am. Chem. Soc., 1995, 117, 3649; R. A. Singer and E. Carreira, J. Am. Chem. Soc., 1995, 117, 12360; H. J. Knolker and H. Hermann, Angew. Chem., Int. Ed. Engl., 1996, 35, 341; D. J. Berrisford and C. Bolm, Angew. Chem., Int. Ed. Engl., 1995, 34, 1717.
5. H. Koshima and T. Matsuura, Kokagaku, 1995, 19, 10; H. Koshima, Y. Chisaka, Y. Wang, X. Yao, H. Wang, R. Wang, A. Maeda and T. Matsuura, Tetrahedron, 1994, 50, 13 617; H. Koshima, K. Ding and T. Matsuura, J. Chem. Soc. Chem Commun., 1994, 2053; H. Koshima, K. Ding, Y. Chisaka and T. Matsuura, Tetrahedron: Asymmetry, 1995, 6, 101; H. Koshima, K. Ding, Y. Chisaka, T. Matsuura, Y. Ohashi and M. Mukasa, J. Org. Chem., 1996, 61, 2352; H. Koshima, K. Ding, Y. Chisaka and T. Matsuura, J. Am. Chem. Soc., 1996, 118, 12 059.