Transition-Metal-Free Activation of Amides by N−C Bond Cleavage

Guangchen Li, Michal Szostak

Research output: Contribution to journalReview articlepeer-review

46 Scopus citations

Abstract

The amide bond N−C activation represents a powerful strategy in organic synthesis to functionalize the historically inert amide linkage. This personal account highlights recent remarkable advances in transition-metal-free activation of amides by N−C bond cleavage, focusing on both (1) mechanistic aspects of ground-state-destabilization of the amide bond enabling formation of tetrahedral intermediates directly from amides with unprecedented selectivity, and (2) synthetic utility of the developed transformations. Direct nucleophilic addition to amides enables a myriad of powerful methods for the formation of C−C, C−N, C−O and C−S bonds, providing a straightforward and more synthetically useful alternative to acyl-metals.

Original languageEnglish (US)
Pages (from-to)649-659
Number of pages11
JournalChemical Record
Volume20
Issue number7
DOIs
StatePublished - Jul 1 2020

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Biochemistry
  • Chemical Engineering(all)
  • Materials Chemistry

Keywords

  • N−C activation
  • amides
  • metal-free
  • tetrahedral intermediates
  • transamidation

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