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ELECTROCHEMISTRY

Bringing amines back into aziridination

Nature Chemistry volume 13, pages 1027–1028 (2021)Cite this article

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Aziridines — three-membered nitrogen-containing heterocycles — are important synthetic targets, but N-alkyl aziridines are difficult to synthesize. Now, an electrochemical method, involving a dicationic intermediate, enables the coupling of alkenes and amines.

Since initially described by Gabriel in 1888 (ref. 1), aziridines have fascinated chemists2. This fascination is partly due to the reactivity of this nitrogen-containing three-membered heterocycle — their bond strain means aziridines are often described as “spring-loaded” — to ring opening reactions. This reactivity is a feature of the biological activity of aziridine-containing natural products, which often exhibit cytotoxicity related to alkylation reaction in vivo.

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Fig. 1: Development of a new strategy for aziridination synthesis.

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  1. Process Research and Development, Merck & Co., Inc., Rahway, NJ, USA

    Tiffany Piou & Louis-Charles Campeau

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  1. Tiffany Piou
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  2. Louis-Charles Campeau
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Correspondence to Louis-Charles Campeau.

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The authors declare no competing interests.

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Piou, T., Campeau, LC. Bringing amines back into aziridination. Nat. Chem. 13, 1027–1028 (2021). https://doi.org/10.1038/s41557-021-00819-7

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  • DOI: https://doi.org/10.1038/s41557-021-00819-7

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