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. 2016 Jun 6;55(24):6959-63.
doi: 10.1002/anie.201601914. Epub 2016 Apr 21.

Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage

Shicheng Shi  1 , Guangrong Meng  1 , Michal Szostak  2
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Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage

Shicheng Shi et al. Angew Chem Int Ed Engl. .

Abstract

The first Ni-catalyzed Suzuki-Miyaura coupling of amides for the synthesis of widely occurring biaryl compounds through N-C amide bond activation is reported. The reaction tolerates a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents on both coupling partners. The reaction constitutes the first example of the Ni-catalyzed generation of aryl electrophiles from bench-stable amides with potential applications for a broad range of organometallic reactions.

Keywords: N−C activation; amide bonds; biaryls; cross-coupling; nickel.

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