Lithium hydride is efficiently used as a reducing agent in the ligated Ni0 catalysed homocoupling of aryl bromides and chlorides.
References
1.
AntonU., GöltnerC., and MullenK., Chem. Ber., 1992, 125, 2325.
2.
LipschutzB. H., MüllerP., and LeinweberD., Tetrahedron Lett., 1999, 40, 3677.
3.
MamikawaK., WatanabeT., and UemuraM., J. Org. Chem1996, 61, 1375.
4.
(a) YamamotoT., MoritaA., MiyazakiY., MaruyamaT., WakayamaH., ZhouZ. H., NakamuraY., KanbaraT., SasakiS., and KubotaK., 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.
(a) MiyauraN., and SuzukiA., Chem. Rev., 1995, 95, 2457; (b) V. Farina, Pure Appl. Chem., 1996, 68, 73.
7.
(a) SemmelhackM. F., HelquistP. M., JonesL. D., KellerL., MendelsonL., RyonoL. S., SmithJ. G., and StaufferR. D., 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.
CaubèreP., 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.
LourakM., VanderesseR., FortY., and CaubèreP., 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.
FortY., Tetrahedron Lett., 1995, 36, 6051.
11.
Ligated Ni0 reagents were found to be very efficient in desulfurization of various sulfur containing compounds: (a) BeckerS., FortY., VanderesseR., and CaubereP., 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: IllyS., TillementO., MachizaudF., DuboisJ. M., MassicotF., FortY., and GhanbajaJ., Philas. Mag. A, 1999, 79, 1021.