Chemo-selective Aziridination and Oxyamination of Alkenes with Nano-cobalt catalyst

Aziridine synthesis from readily available alkene has been a long-standing point of interest for organic chemists, owing to the widely existence in bioactive compounds and plentiful synthetic derivatizations of aziridines. Compared with using iminoiodinane or azide as the nitrogen source, the seeking for catalytic systems employing novel nitrogen transfer reagent under external oxidant-free conditions are the cutting-edge techniques in this field. Herein, a pioneering nano-cobalt catalyzed chemo-selective aziridination/oxyamination reaction from alkene and hydroxylamine is developed, this system proceeds without external oxidant and exhibits mild, efficient, atom-economic and recyclable characters. Late-stage aziridinations of drug-derived alkenes and diversified synthetic transformation of the aziridine product further expands the utility of this method. Moreover, this novel methodology represents a rare example of alkene difunctionalization under nano-catalyst, which bridges the gap between homo- and heterogeneous catalysis. Moreover, the full characterizations of the nano-cobalt catalyst and mechanistic studies including deuterium-labeled experiment and Hammet analysis were conducted, while a reasonable mechanism was also suggested accordingly.