Chemical Society Reviews· 2012Q1· Review
Organocatalytic umpolung: N-heterocyclic carbenes and beyond
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- Q1SCImago
- 2012year
Short summary
N-heterocyclic carbenes (NHCs) enable organocatalytic umpolung by acting as acyl anion equivalents, a strategy that has since been expanded to other organocatalyst families.
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Key points
- Umpolung reverses innate polarity-driven reactivity in organic molecules.
- N-heterocyclic carbenes (NHCs) were the first organocatalysts to achieve umpolung by generating acyl anion equivalents.
- NHC-catalyzed reactions have seen extensive development since their introduction.
- Other organocatalyst families are now also capable of mediating umpolung transformations.
AI-generated from the title and abstract; the full text is not read.
Abstract
The umpolung strategy encompasses all the methods that make organic molecules react in an inverse manner compared to their innate polarity-driven reactivity. This concept entered the field of organocatalysis when it was recognized that N-heterocyclic carbenes (NHCs) can provide catalytic access to acyl anion equivalents. Since then, tremendous efforts have followed to develop a broad variety of NHC-catalyzed reactions. In addition to this, more recent research developments have shown that other families of organocatalysts are also able to mediate transformations in which inversion of polarity is involved. This tutorial review aims at offering a didactic overview of organocatalytic umpolung and should serve as an inspiration for further progress in this field.
The authors' abstract, as published at the source. Chemical Society Reviews, 2012 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry