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Issue 9, 2012
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Organocatalytic umpolung: N-heterocyclic carbenes and beyond

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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.

Graphical abstract: Organocatalytic umpolung: N-heterocyclic carbenes and beyond

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The article was received on 04 Dec 2011 and first published on 29 Feb 2012

Article type: Tutorial Review
DOI: 10.1039/C2CS15333E
Chem. Soc. Rev., 2012,41, 3511-3522

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    Organocatalytic umpolung: N-heterocyclic carbenes and beyond

    X. Bugaut and F. Glorius, Chem. Soc. Rev., 2012, 41, 3511
    DOI: 10.1039/C2CS15333E

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