Issue 3, 2023

Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide

Abstract

N-heterocycles are prominent structural motifs frequently occurring in organic synthesis and applications. Therefore, straightforward and green synthesis methods using common starting materials like alkenes are highly desired. Here, the metal-free electrochemical coupling of aromatic olefins with NH3 and CO2 or CS2 in a telescoped sequence is reported, forming 2-oxazolidinones or 2-thiazolidinethiones. The reaction proceeds via a N–H aziridine, which subsequently undergoes ring expansion with CO2 or CS2. Both steps are mediated by the same simple iodide catalyst and total yields of up to 91% referring to the alkene are achieved with excellent regioselectivities. This sustainable reaction using readily available materials possesses an excellent atom efficiency with only H2 as a potentially useful by-product.

Graphical abstract: Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide

Supplementary files

Article information

Article type
Paper
Submitted
17 10 2022
Accepted
17 1 2023
First published
19 1 2023

Green Chem., 2023,25, 978-985

Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide

J. R. Vanhoof, R. Dirix and D. E. De Vos, Green Chem., 2023, 25, 978 DOI: 10.1039/D2GC03879J

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