Kumada-Corriu coupling reaction

Table 4.8 Comparison of rate constants for a series of Kumada-Corriu coupling reactions in flow reactors with corresponding batch reaction [2],...

Ni(0) carbenes are also effective for the Kumada-Corriu coupling reaction between aryhnagnesium reagents and aryl chlorides or fluorides in ca. 35 catalytic turnovers (equation 5). The yields are generally high even at room temperature (ca. 30 turnovers over 18h) only when the aryl chloride is congested (substituents ortho to Cl) does the yield suffer. It is noteworthy, however, that very similar yields were obtained when the N-heterocarbene ligands were replaced by t-BusP. 

An extensive survey of various NHCs has allowed the development of a nickel-catalysed three-component coupling of benzaldehyde, norbornene, and trialkylsilane. The NHC (12) proved to be the most effective. The Kumada-Corriu coupling reaction of aryl bromides with t-butylmagnesium chloride has been reported to be more efficiently carried out in the presence of an NHC ligand bearing a pendant carboxylic group such as the one derived from (13). ... 

Wolf, J., Labande, A., Daran, J.C. and Poli, R., Nickel(ll) conplexes with bifunctional phosphine-imidazolium ligands and their catal)4ic activity in the Kumada-Corriu coupling reaction, J. Organomet. Chem. 691 (3), 433 43 (2006). 

Scheme 2.45 Transition metal-mediated activation of the aromatic carbon—fluorine bond and subsequent reactions. Ahoue stoichiometric reaction of electron-deflclent fluoroarenes with NI(0) complexes [101]. Belou Ni(0) carbene-catalyzed Kumada-Corriu coupling between fluoroarenes and aryl Grignard compounds [102].

NHC-Ni-Catalyzed Corriu-Kumada Cross-Coupling Reactions... 

In a Kumada-Corriu reaction, an aryl halide is oxidatively coupled with a homogeneous nickel(ll)-phosphine catalyst [2], This species reacts with a Grignard reagent to give biaryl or alkylaryl compounds. Later, palladium-phosphine complexes were also successfully applied. By this means, stereospecific transformations were achieved. 

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 1971, a year before the groups of Corriu and Kumada [5] independently reported the groundbreaking work on the topic of nickel-catalyzed cross-coupling reactions of aryl and vinyl halides with Grignard reagents, Tamura and Kochi described an iron-catalyzed vinylation reaction of Grignard reagents with vinyl halides (Scheme 5.1) [6]. 

Since the discovery of transistion metal-catalyzed cross-coupling reactions by the groups of Kochi, Kumada and Corriu in the early 1970s, impressive progress has been achieved in the development of these methods into a synthetically indispensable... 

Cross-coupling reactions 5-alkenylboron boron compounds, 9, 208 with alkenylpalladium(II) complexes, 8, 280 5-alkylboron boron, 9, 206 in alkyne C-H activations, 10, 157 5-alkynylboron compounds, 9, 212 5-allylboron compounds, 9, 212 allystannanes, 3, 840 for aryl and alkenyl ethers via copper catalysts, 10, 650 via palladium catalysts, 10, 654 5-arylboron boron compounds, 9, 208 with bis(alkoxide)titanium alkyne complexes, 4, 276 carbonyls and imines, 11, 66 in catalytic C-F activation, 1, 737, 1, 748 for C-C bond formation Cadiot-Chodkiewicz reaction, 11, 19 Hiyama reaction, 11, 23 Kumada-Tamao-Corriu reaction, 11, 20 via Migita-Kosugi-Stille reaction, 11, 12 Negishi coupling, 11, 27 overview, 11, 1-37 via Suzuki-Miyaura reaction, 11, 2 terminal alkyne reactions, 11, 15 for C-H activation, 10, 116-117 for C-N bonds via amination, 10, 706 diborons, 9, 167... 

Fig. 3 Hiyama, Kumada-Corriu, Stille, Sonogashira, and other nickel-catalyzed coupling reactions...

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