Suzuki aryl couplings mediated by phosphine-free nickel complexes

Tetrahedron

Volumn 55, Issue 40, 1999, Pages 11889-11894

  Leadbeater, Nicholas E ^a   Resouly, Sarah M ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Biaryls; Coupling reactions; Nickel and compounds; Suzuki reactions

Indexed keywords

NICKEL; PHOSPHINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; LIGAND BINDING; PRIORITY JOURNAL;

EID: 0033214646     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00676-6     Document Type: Article

References (17)

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3. a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
4. b) Suzuki, A. Pure Appl. Chem. 1994, 66, 213.
5. c) Martin, A.R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
6. d) Suzuki, A. Acc. Chem. Res. 1992, 15, 178.
7. Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
8. See for example: a) Diederich. F.; Stang. P. Eds. Metal-Catalysed Cross-Coupling Reactions; Wiley-VCH; Weinheim, 1998.
9. b) Miller, J.A.; Farrell, R.P. Tetrahedron Lett. 1998, 39, 6441.
10. c) Schunn, R.A. Inorg. Chem. 1976, 15, 208.
11. d) Saito, S.; Oh-Tani, S.; Miyaura, N. J. Org. Chem. 1997, 62, 8024.
12. A.F. Indolese, Tetrahedron Lett., 1997, 38, 3513.
13. 2Ni C, 42.0; H, 2.9; Cl 24.9. Found: C, 42.0; H, 2.8; Cl 24.5.
14. 2Ni: C, 43.4; H, 9.1; Cl 21.3. Found: C, 43.3; H, 9.3; Cl 21.4.
15. a) Semmelhack, M.F.; Helquist P.M.; Jones, L.D. J. Am. Chem. Soc. 1971, 93, 5908.
16. b) Negishi, E.-I. Acc. Chem. Res. 1982, 15, 340.
17. It is likely that Ni(I) and Ni(III) intermediates with geometries ranging from square planar through tetrahedral to octahedral may well be involved in the reaction mechanism. Furthermore, the very different hybridisation and bite angle of the two ligands will undoubtedly play a role in determining the rate of reaction.