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

Shicheng Shi; Guangrong Meng; Michal Szostak

doi:10.1002/anie.201601914

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

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

Authors

Shicheng Shi¹, Guangrong Meng¹, Michal Szostak²

Affiliations

¹ Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ, 07102, USA.
² Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ, 07102, USA. michal.szostak@rutgers.edu.

PMID: 27101428
DOI: 10.1002/anie.201601914

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.