Tamao-Kumada-Corriu Cross-Coupling Reaction

Scheme 1.12 (a) General conditions for the Tamao-Kumada-Corriu cross-coupling reaction, (b) The proposed mechanism for the Tamao-Kumada-Corriu cross-coupling arylation procedure (note the base used is an alkoxide or hydroxide) [12a]. 

Scheme 1.13 The enantioselective catalytic variant of the Tamao-Kumada-Corriu cross-coupling reaction as developed by Hayashi et al. [30].

Tamao-Kumada-Corriu Cross-Coupling Reaction... 

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... 

After Kumada and Tamao and Corriu independently reported the nickel(II) salts-and complexes-catalyzed cross-coupling reaction of Grignard reagents with aryl and alkenyl halides, the Pd-catalyzed reaction of Grignard reagents was first reported by Murahashi. ... 

Silicon, an element widely used in many facets of organic chemistry [7], was not effectively employed in cross-coupling reactions until 16 years after the first reported transition-metal-catalyzed coupling reactions by Corriu, Kumada, and Tamao [8], Most early developments in this field were achieved by the use of organoboron (1979) [9], organozinc (1977) [10], and organotin (1977) [11] coupling partners (Scheme 7.1). 

A cross-coupling arylation procedure was developed independently in 1972 by Tamao and Kumada in Japan and Corriu in France and is known as the Tamao-Kumada-Corriu cross-rxtupling reaction... 

The nickel-catalyzed reaction of Grignard reagent with an aryl halide, widely known as Corriu-Kumada-Tamao (CKT), constituted the first example of efficient cross-coupling reaction of aryl halides. However, the elassical protocol was not properly optimized and recent improvements have been achieved using NHC-Ni complexes. 

The history of the discoveries and developments of the palladium-catalyzed crosscoupling reactions has been documented in many reviews, book chapters, and monographs. Palladium-catalyzed processes can be traced back to Nickel-catalyzed cross-coupling reactions of organomagnesium derivatives reported in 1972 by Tamao, Sumitani, and Kumada as well as by Corriu and Masse. Some groups led by Murahashi et Fauvarque, and Sekiya and Ishikawa independently... 

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