Kumada coupling reaction, M = catalyst, usually based on Ni or Pd complexes
In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972.[1][2]
The reaction is notable for being among the first reported catalytic cross-coupling methods. Despite the subsequent development of alternative reactions (Suzuki, Sonogashira, Stille, Hiyama, Negishi), the Kumada coupling continues to be employed in many synthetic applications, including the industrial-scale production of aliskiren, a hypertension medication, and polythiophenes, useful in organic electronic devices.
^Corriu, R. J. P.; Masse, J. P. (1 January 1972). "Activation of Grignard reagents by transition-metal complexes. A new and simple synthesis of trans-stilbenes and polyphenyls". Journal of the Chemical Society, Chemical Communications (3): 144a. doi:10.1039/C3972000144A.
^Tamao, Kohei; Sumitani, Koji; Kumada, Makoto (1 June 1972). "Selective carbon–carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes". Journal of the American Chemical Society. 94 (12): 4374–4376. doi:10.1021/ja00767a075.
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