Cross-Coupling of Amides by N-C Bond Activation

Guangrong Meng, Shicheng Shi, Michal Szostak

Research output: Contribution to journalArticlepeer-review

200 Scopus citations


In recent years, significant conceptual advances have taken place in the field of amide bond cross-coupling. Mild and selective functionalization of amides by transition-metal catalysis has an enormous potential for widespread applications in both industry and academia due to the unparalleled prevalence of amide-containing molecules. However, direct metal insertion into the N-C(O) amide bond is extremely difficult as a consequence of amidic resonance. In this account, we summarize our work on the development of new cross-coupling reactions of amides by N-C bond activation, and briefly discuss other modern developments in this area. 1 Introduction 2 Amide Bond Ground-State Distortion 3 Acyl Amide N-C Cross-Coupling 3.1 Suzuki Cross-Coupling 3.2 Negishi Cross-Coupling 3.3 Esterification and Amidation via N-C Cross-Coupling 4 Decarbonylative Amide N-C Cross-Coupling 4.1 Heck Cross-Coupling 4.2 Suzuki Cross-Coupling 4.3 C-H Activation 4.4 Decarbonylative Borylation 5 Transition-Metal-Free Activation of Amide Bonds 6 Mechanistic Studies 7 Conclusions and Outlook.

Original languageEnglish (US)
Article numberst-2016-a0521-a
Pages (from-to)2530-2540
Number of pages11
Issue number18
StatePublished - Nov 14 2016

All Science Journal Classification (ASJC) codes

  • Organic Chemistry


  • C-H activation
  • N-C bond activation
  • Suzuki coupling
  • amides
  • cross-coupling
  • decarbonylative coupling
  • nickel
  • palladium


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