Cross nickel-catalyzed

Optically active amine-thioether ligands (492) have been investigated in nickel-catalyzed asymmetric cross-coupling reactions of Grigard reagents.1338... 

Activated aryl chlorides, which are close in reactivity to unactivated aryl bromides, underwent reaction with the original P(o-tol)3-ligated catalyst.58 Nickel complexes, which catalyze classic C—C bond-forming cross-couplings of aryl chlorides, 9-64 also catalyzed aminations of aryl chlorides under mild conditions.65,66 However, the nickel-catalyzed chemistry generally occurred with lower turnover numbers and with a narrower substrate scope than the most efficient palladium-catalyzed reactions. 

Scheme 6.44 Nickel-catalyzed cross-coupling of zirconocenes and aryl halides.

Cross-coupling reactions of vinyl zirconocenes of general structure 41, mainly using group 10 metal catalysts, can be smoothly effected to give a variety of vinyl selenide-con-taining materials, which are amenable to further elaboration through nickel-catalyzed... 

Other successful examples of catalysts containing NHC ligands are found in palladium- and nickel-catalyzed carbon-carbon bond formations. The catalyst development with these metals has focused in particular on Heck-type reactions, especially the Mizoroki-Heck reaction itself [Eq. (42)] and various cross coupling reactions [Eq. (43)], e.g., the Suzuki-Miyaura reaction ([M] = and the Kumada-Corriu reaction ([M] = MgBr). " Related reactions like the Sonogashira coupling [Eq. (44)]326-329 Buchwald-... 

In the late 1970s and early 1980s, Kumada described nickel-catalyzed asymmetric cross-coupling reactions of 1-arylethylmagnesium chlorides with vinyl bromide in... 

Figure 3.49. Chiral ligands that exhibit high enantioselectivity in the nickel-catalyzed Grignard cross-coupling reaction of vinyl bromide (or chloride) with 1-phenylethylmagne-sium chloride.

Scheme 17.41 Nickel-catalyzed cross-coupling of phenol-derived sulfamate esters.

Asymmetric Grignard Cross-Coupling Catalyzed by Chiral Phosphine-Nickel Complexes 73)... 

More recent review Hayashi, T. Asymmetric Grignard Cross-Coupling Catalyzed by Chiral Phosphine-Nickel and Phosphine-Palladium Complexes, in Asymmetric Reactions and Processes in Chemistry (Eliel, E. L., Otsuka, S. ed.), American Chemical Soc. Symp. Series Vol. 185, p. 177 (1982)... 

SCHEME 108. Nickel-catalyzed cross-coupling reactions... 

Palladium- or nickel-catalyzed cross-coupling reactions with organozincs and related organometals... 

---