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

06 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Aziridine synthesis from readily available alkene has been a long-standing point of interest for organic chemists, owing to their widely existence in bioactive compounds and plentiful synthetic derivatiza-tions. Herein, a nano-cobalt catalyzed chemo-selective aziridina-tion/oxyamination reaction from alkene and hydroxylamine was de-veloped under room temperature, this system proceeds without exter-nal oxidant and exhibits mild, efficient, atom-economic and recyclable characters, which makes this discovery more practical and fascinating. Late-stage aziridinations of drug-derived olefins and diversified syn-thetic transformation of the aziridine product further expanded 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. Finally, mechanistic studies including deuterium-labeled experiment and Hammet analysis were conducted, and a potential mechanism was proposed accordingly.

Keywords

alkene
aziridination
oxyamination
heterogeneous cobalt
hydroxylamine

Supplementary materials

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Title
Supporting Information of Chemo-selective Aziridination and Oxyamination of Alkenes with Nano-cobalt catalyst
Description
Additional experimental details, materials, methods, and 1H, 13C ,19F NMR spectra for all compounds.
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