Lithium Hydride Mediated Nickel(0) Catalysed Biaryl Synthesis from Aryl Chlorides and Bromides

Abstract

Lithium hydride is efficiently used as a reducing agent in the ligated Ni⁰ catalysed homocoupling of aryl bromides and chlorides.

References

1. U. Anton, C. Göltner and K. Mullen, Chem. Ber., 1992, 125, 2325.
2. B. H. Lipschutz, P. Müller and D. Leinweber, Tetrahedron Lett., 1999, 40, 3677.
3. K. Mamikawa, T. Watanabe and M. Uemura, J. Org. Chem., 1996, 61, 1375.
4. (a) T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, Z. H. Zhou, Y. Nakamura, T. Kanbara, S. Sasaki and K. Kubota, Macromolecules, 1992, 25, 1214; (b) S. S. Zhu and T. M. Swager, Adv. Mater., 1996, 8, 497; (c) N. E. Leadbeater and S. M. Resouly, Tetrahedron Lett., 1999, 40, 4243.
5. (a) F. Ullmann, Ber., 1903, 36, 2389; (b) E. Fanta, Synthesis, 1974, 1, 9.
6. (a) N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; (b) V. Farina, Pure Appl. Chem., 1996, 68, 73.
7. (a) M. F. Semmelhack, P. M. Helquist, L. D. Jones, L. Keller, L. Mendelson, L. S. Ryono, J. G. Smith and R. D. Stauffer, J. Am. Chem. Soc., 1981, 103, 6460; (b) L. Colon and D. R. Kelsey, J. Org. Chem., 1986, 51, 2627; (c) A. Jutand and A. Mosleh, Synlett, 1993, 568; (d) V. Percec, J. Y. Bae, M. Zhao and D. H. Hill, J. Org. Chem., 1995, 60, 1060 and 1066; (e) H. A. Reisch, V. Enkelmann and U. Scherf, J. Org. Chem., 1999, 64, 655.
8. (a) P. Caubère, Pure Appl. Chem., 1985, 57, 1875; (b) P. Caubère, Rev. Heteroat. Chem., 1991, 4, 79; (c) P. Gallezot, C. Leclercq, Y. Fort and P. Caubère, J. Mol. Catal., 1994, 93, 79.
9. (a) M. Lourak, R. Vanderesse, Y. Fort and P. Caubère, J. Org. Chem., 1989, 54, 4840; (b) M. Lourak, R. Vanderesse, Y. Fort and P. Caubère, J. Org. Chem., 1989, 54, 4844; (c) Y. Fort, S. Becker and P. Caubère, Tetrahedron., 1994, 50, 11893.
10. Y. Fort, Tetrahedron Lett., 1995, 36, 6051.
11. Ligated Ni⁰ reagents were found to be very effcient in desulfurization of various sulfur containing compounds: (a) S. Becker, Y. Fort, R. Vanderesse and P. Caubere, J. Org. Chem., 1989, 54, 4848; (b) S. Becker, Y. Fort and P. Caubere, J. Org. Chem., 1990, 55, 6194; (c) C. Kuehm-Caubere, A. Guilmart, S. Adach-Becker, Y. Fort and P. Caubere, Tetrahedron Lett., 1998, 39, 8987.
12. In the presence of LiCl, the catalyst is difficult to prepare. Moreover, generation of our catalyst from NiCl₂ is more difficult than from Ni(OAc)₂: S. Illy, O. Tillement, F. Machizaud, J. M. Dubois, F. Massicot, Y. Fort and J. Ghanbaja, Philas. Mag. A, 1999, 79, 1021.