First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

Rocco, Daniele, Folgueiras Amador, Ana, Brown, Richard C.D. and Feroci, Marta (2022) First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell. Beilstein Journal of Organic Chemistry, 18, 979-990. (doi:10.3762/bjoc.18.98).

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Abstract

In this paper we present the first electrochemical generation of NHC carried out in a divided flow cell. The flow cell operated in the recycle mode. The need for a divided cell derived from the anodic electroactivity of the electrogenerated carbene. In order to have NHC accumulation in the catholyte, the Nafion membrane (cell separator) was pretreated with an alkaline solution. The formation of NHC was quantified as its reaction product with elemental sulfur. The NHC was successfully used as organocatalyst in two classical umpolung reactions of cinnamaldehyde: its cyclodimerization and its oxidative esterification.

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Accepted/In Press date: 29 July 2022

Published date: 5 August 2022

Additional Information: Funding Information: D.R. thanks the Sapienza University for a Ph.D. grant. The authors acknowledge financial support from EPSRC (Photo-Electro Programme Grant EP/P013341/1). Publisher Copyright: © 2022 Rocco et al.; licensee Beilstein-Institut.

Keywords: Breslow intermediate, N-heterocyclic carbene, cathodic reduction, flow electrochemistry, oxidative esterification