Nickel catalyzed cross Negishi coupling

E. -i. Negishi, F. Liu, Palladium- or Nickel-catalyzed Cross-coupling with Organometals Containing Zinc, Magnesium, Aluminium, and Zirconium, in Metal-catalyzed Cross-coupling Reactions, Eds. F. Diederich, P. J. Stang, Wiley-VCH, Weinheim, 1998, 1—42. 

Negishi El (1982) Palladium-catalyzed or nickel-catalyzed cross- coupling - a new selective method for carbon-carbon bond formation. Acc Chem Res 15 340-348... 

Negishi E-I. Palladium- or Nickel-Catalyzed Cross Coupling. A New Selective Method for Carbon-Carbon Bond Formation. Acc. Chem. Res. 1982 15 340-348. 

Negishi, E. Palladium- or nickel-catalyzed cross coupling involving proximally heterofunctional reagents. Curr. Trends Org. Synth., Proc. Int. Conf., 4th 1983, 269-280. 

For a summary on work employing palladium- and nickel-catalyzed cross-coupling processes, see E. Negishi, Acc. Chem. Res. 1982, 15, 340-348. 

Scheme 1.24 Nickel-catalyzed cross-coupling of alane 59 (Negishi, 1976).

E. Negishi, Acc. Chem. Res., 1982, 15, 340-348. Palladium- or Nickel-Catalyzed Cross-Coupling. A New Selective Method for Carbon-Carbon Bond Formation. T. Hayashi and M. Kumada, Acc. Chem. Res., 1982, 15, 395-401. Asymmetric Synthesis Catalyzed by Transition-Metal Complexes with Functionalized Chiral Ferro-cenylphosphine Ligands. 

Negishi, E., Takahashi, T., Baba, S., Van Horn, D. E., Okukado, N. Nickel- or palladium-catalyzed cross coupling. 31. Palladium- or nickel-catalyzed reactions of alkenylmetals with unsaturated organic halides as a selective route to arylated alkenes and conjugated dienes scope, limitations, and mechanism. J. Am. Chem. Soc. 1987,109, 2393-2401. 

Zhou, J., Fu, G. C. Cross-Couplings of Unactivated Secondary Alkyl Halides Room-Temperature Nickel-Catalyzed Negishi Ikyl Bromides and Iodides. J. Am. Chem. Soc. 2003,125, 14726-14727. 

In the area of organometallic chemistry, we begin with a procedure for the palladium-catalyzed animation of aryl halides and aryl triflates, illustrated by syntheses of N-HEXYL-2-METHYL-4-METHOXYANIUNE and N-METHYL-N-<4-CHLOROPHENYL)-ANILINE. The next procedure describes the synthesis of 1,2,3,4-TETRAHYDROCARBAZOLE by the palladium-catalyzed annulation of ketones with o-iodoaniline. Next, a procedure for the synthesis of 2,7-DIMETHYLNAPHTHALENE via the nickel-catalyzed coupling of aryl O-carbamates with Grignard reagents is presented. The fourth procedure in this section describes the synthesis of 5-METHYL-2,2 -BIPYRIDINE by a Negishi cross-coupling reaction... 

For progress on nickel-catalyzed Negishi cross-couplings of aUcyl electrophiles, see Ref. 4. Gao Y, Harada K, Hata T, Urahe H, Sato F (1995) J Org Chem 60 290 Wiskur SL, Korte A, Fu GC (2004) J Am Ghem Soc 126 82... 

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