ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

Electrochemical Aziridination of Internal Alkenes with Primary Amines

preprint
submitted on 18.08.2020 and posted on 25.08.2020 by Maksim Oseka, Gabriele Laudadio, Nicolaas P. van Leest, Marco Dyga, Aloisio de Andrade Bartolomeu, Lukas Goossen, B. de Bruin, Kleber Thiago de Oliveira, Timothy Noel
Aziridines are useful synthetic building blocks, widely employed for the preparation of various nitrogen-containing derivatives. As the current methods require the use of prefunctionalized amines, the development of a synthetic strategy towards aziridines, that can establishe the union of alkenes and amines, would be of great synthetic value. Herein, we report an electrochemical approach, which realizes this concept via an oxidative coupling between alkenes and primary alkyl amines. The reaction is carried out in an electrochemical flow reactor, leading to short reaction times (5 min), high yields and broad scope. At the cathode, hydrogen is generated, which can be used in a second reactor to reduce the aziridine, yielding the corresponding hydroaminated product. Mechanistic investigations and DFT calculations revealed that the alkene is first anodically oxidized and subsequently reacted with the amine coupling partner.

History

Email Address of Submitting Author

t.noel@tue.nl

Institution

Eindhoven University of Technology

Country

The Netherlands

ORCID For Submitting Author

0000-0002-3107-6927

Declaration of Conflict of Interest

no conflict of interest

Exports

Logo branding

Exports