NHC-Activations on α-, β-, γ-, and Beyond

Chem Rec. 2023 Jul;23(7):e202200279. doi: 10.1002/tcr.202200279. Epub 2023 Mar 14.

Abstract

Over the recent decades, due to the special electronic characteristics and diverse reactivities, N-heterocyclic carbene (NHC) has received significant interest in organocatalyzed reactions. The formation of Breslow intermediates by NHC can convert into acyl anion equivalent, enolates, homoenolate, acyl azolium, and vinyl enolate etc., and the cycloaddition reactions of these species has attracted lots of attention. In this review, we focus on the summry of the development of NHC-activation of carbonyl carbon (or imine carbon) in situ, α-, β-, γ-, and beyond, and the cycloaddition reaction of these species.

Keywords: N-heterocyclic carbene (NHC); acyl azolium; enolate; homoenolate; remote activation; vinyl enolate.

Publication types

  • Review

MeSH terms

  • Carbon*
  • Carboxylic Acids*
  • Cycloaddition Reaction
  • Imines

Substances

  • carbene
  • Carbon
  • Carboxylic Acids
  • Imines