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 products^1,2,3, and, in some cases, the aziridine functional group itself imbues important biological (for example, anti-tumour) activity^4,5,6. 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.

氮丙啶——三元含氮环状分子——是重要的合成目标。它们巨大的环张力和由此产生的开环反应倾向使它们成为多种胺产品的多功能前体^1,2,3，并且在某些情况下，氮丙啶官能团本身具有重要的生物学（例如，抗肿瘤）活性^{4 ,5,6}. 将普遍存在的烯烃转化为氮丙啶是一种有吸引力的合成策略，但通常使用亲电氮源而不是广泛使用的胺亲核试剂来完成。在这里，我们表明未活化的烯烃可以电化学转化为亚稳态双阳离子中间体，该中间体在碱性条件下与伯胺发生氮丙啶化反应。相对于通过现有最先进方法获得的产品，这种新方法扩大了易于获得的N-烷基氮丙啶产品的范围。这种方法的一个关键战略优势是氧化烯烃活化与氮丙啶化步骤分离，从而实现了广泛的商业化但对氧化敏感的⁷胺作为这种应变诱导转化的偶联伙伴。更广泛地说，我们的工作为使用这种双阳离子池方法的各种双官能化反应奠定了基础。