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

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...

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Autores principales: Rocco, Daniele, Folgueiras-Amador, Ana A, Brown, Richard C D, Feroci, Marta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9359202/
https://www.ncbi.nlm.nih.gov/pubmed/35965857
http://dx.doi.org/10.3762/bjoc.18.98
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author Rocco, Daniele
Folgueiras-Amador, Ana A
Brown, Richard C D
Feroci, Marta
author_facet Rocco, Daniele
Folgueiras-Amador, Ana A
Brown, Richard C D
Feroci, Marta
author_sort Rocco, Daniele
collection PubMed
description 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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spelling pubmed-93592022022-08-12 First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell Rocco, Daniele Folgueiras-Amador, Ana A Brown, Richard C D Feroci, Marta Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2022-08-05 /pmc/articles/PMC9359202/ /pubmed/35965857 http://dx.doi.org/10.3762/bjoc.18.98 Text en Copyright © 2022, Rocco et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Rocco, Daniele
Folgueiras-Amador, Ana A
Brown, Richard C D
Feroci, Marta
First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
title First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
title_full First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
title_fullStr First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
title_full_unstemmed First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
title_short First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
title_sort first example of organocatalysis by cathodic n-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9359202/
https://www.ncbi.nlm.nih.gov/pubmed/35965857
http://dx.doi.org/10.3762/bjoc.18.98
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