Palladium-catalyzed amination of aromatic halides in water-containing solvent systems: a two-phase protocol

Abstract

The use of the six-fold sulfonated ligand BINAS-6 1 permits the Pd⁰-catalyzed amination of aromatic halides in water containing single- or two-phase systems.

References

1. M. Kosugi, M. Kameyama and T. Migita, Chem. Lett., 1983, 927; M. Kosugi, M. Kameyama and T. Migita, Nippon Kagaku Kaishi, 1985, 3, 547.
2. A. S. Guram, R. A. Rennels and S. L. Buchwald, Angew. Chem., 1995, 107, 1456; Angew. Chem., Int. Ed. Engl., 1995, 34, 1348; J. P. Wolfe, R. A. Rennels and S. L. Buchwald, Tetrahedron, 1996, 52, 7525; J. P. Wolfe, S. Wagaw and S. L. Buchwald, J. Am. Chem. Soc., 1996, 118, 7215; S. Wagaw and S. L. Buchwald, J. Org. Chem., 1996, 61, 7240 palladium-catalyzed aminations of triflate-arenes J. P. Wolfe and S. L. Buchwald, J. Org. Chem., 1996, 61, 1133; J. P. Wolfe and S. L. Buchwald, J. Org. Chem., 1997, 62, 1264.
3. J. Louie and J. F. Hartwig, Tetrahedron Lett., 1995, 36, 3609; M. S. Driver and J. F. Hartwig, J. Am. Chem. Soc., 1996, 118, 7217; J. Louie, M. S. Driver, B. C. Hamann and J. F. Hartwig, J. Org. Chem., 1997, 62, 1268.
4. See also M. Beller, T. M. Riermeier, C.-P. Reisinger and W. A. Herrmann, Tetrahedron Lett., 1997, 38, 2073; N. P. Reddy and M. Tanaka, Tetrahedron Lett., 1997, 38, 4807.
5. B. Cornils, Angew. Chem., 1995, 107, 1709; Angew. Chem., Int. Ed. Engl., 1995, 34, 1575.
6. W. A. Herrmann and C. W. Kohlpaintner, Angew. Chem., 1993, 105, 1588; Angew. Chem., Int. Ed. Engl., 1993, 32, 1524; P. Kalck and F. Monteil, Adv. Org. Chem., 1992, 34, 219.
7. T. Prinz, W. Keim and B. Drieβen-Hölscher, Angew. Chem., 1996, 108, 1835; Angew. Chem., Int. Ed. Engl., 1996, 35, 1708.
8. W. Keim, Chem Ing. Tech., 1984, 56, 850; G. Mercier and P. Chabardes, Pure Appl. Chem., 1994, 66, 1509; Y. Tokitoh, N. Yoshimura, T. Higashi, K. Mino and M. Murasawa, EP 436226, 1991; Chem. Abstr., 1991, 115, 158508z; A. Behr and W. Keim, Arab. J. Sci. Eng., 1985, 10, 377.
9. H. Bahrmann, K. Bergrath, H.-J. Kleiner, P. Lappe, C. Naumann, D. Peters and D. Regnat, J. Organomet. Chem., 1996, 520, 97.
10. H. S. Bien, J. Stawitz and K. Wunderlich, Ullmann's Encyclopedia of Industrial Chemistry, VCH, Weinheim, 1985, vol. A2, p. 355.