Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication.

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

SUBMITTER: Holst DE 

PROVIDER: S-EPMC9632649 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature