Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication

Dylan E. Holst, Diana J. Wang, Min Ji Kim, Ilia A. Guzei and Zachary K. Wickens ()
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Dylan E. Holst: University of Wisconsin–Madison
Diana J. Wang: University of Wisconsin–Madison
Min Ji Kim: University of Wisconsin–Madison
Ilia A. Guzei: University of Wisconsin–Madison
Zachary K. Wickens: University of Wisconsin–Madison

Nature, 2021, vol. 596, issue 7870, 74-79

Abstract: Abstract Aziridines—three-membered nitrogen-containing cyclic molecules—are important synthetic targets. Their substantial ring strain and resultant proclivity towards ring-opening reactions makes them versatile precursors of diverse amine products1–3, and, in some cases, the aziridine functional group itself imbues important biological (for example, anti-tumour) activity4–6. Transformation of ubiquitous alkenes into aziridines is an attractive synthetic strategy, but is typically accomplished using electrophilic nitrogen sources rather than widely available amine nucleophiles. Here we show that unactivated alkenes can be electrochemically transformed into a metastable, dicationic intermediate that undergoes aziridination with primary amines under basic conditions. This new approach expands the scope of readily accessible N-alkyl aziridine products relative to those obtained through existing state-of-the-art methods. A key strategic advantage of this approach is that oxidative alkene activation is decoupled from the aziridination step, enabling a wide range of commercially available but oxidatively sensitive7 amines to act as coupling partners for this strain-inducing transformation. More broadly, our work lays the foundations for a diverse array of difunctionalization reactions using this dication pool approach.

Date: 2021
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DOI: 10.1038/s41586-021-03717-7

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