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 Okt. 2022
Accepted
17 Janv. 2023
First published
19 Janv. 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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