Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

Electrochemical Friedel–Crafts-type amidomethylation was successfully carried out by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborates, such as iPr(2)NHEtBF(4). Constant current electrolysis of 1,3,5-trimethoxybenzene or indoles in DMA contai...

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Autores principales: Senboku, Hisanori, Hayama, Mizuki, Matsuno, Hidetoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443422/
https://www.ncbi.nlm.nih.gov/pubmed/36105724
http://dx.doi.org/10.3762/bjoc.18.105
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author Senboku, Hisanori
Hayama, Mizuki
Matsuno, Hidetoshi
author_facet Senboku, Hisanori
Hayama, Mizuki
Matsuno, Hidetoshi
author_sort Senboku, Hisanori
collection PubMed
description Electrochemical Friedel–Crafts-type amidomethylation was successfully carried out by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborates, such as iPr(2)NHEtBF(4). Constant current electrolysis of 1,3,5-trimethoxybenzene or indoles in DMA containing 0.1 M iPr(2)NHEtBF(4) using an undivided cell equipped with a Pt plate cathode and a Pt wire anode (a quasi-divided cell) resulted in selective formation of N-acyliminium ions of DMA at the anode, which reacted with arenes to give the corresponding amidomethylated products in good to high yields.
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spelling pubmed-94434222022-09-13 Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate Senboku, Hisanori Hayama, Mizuki Matsuno, Hidetoshi Beilstein J Org Chem Letter Electrochemical Friedel–Crafts-type amidomethylation was successfully carried out by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborates, such as iPr(2)NHEtBF(4). Constant current electrolysis of 1,3,5-trimethoxybenzene or indoles in DMA containing 0.1 M iPr(2)NHEtBF(4) using an undivided cell equipped with a Pt plate cathode and a Pt wire anode (a quasi-divided cell) resulted in selective formation of N-acyliminium ions of DMA at the anode, which reacted with arenes to give the corresponding amidomethylated products in good to high yields. Beilstein-Institut 2022-08-18 /pmc/articles/PMC9443422/ /pubmed/36105724 http://dx.doi.org/10.3762/bjoc.18.105 Text en Copyright © 2022, Senboku 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 Letter
Senboku, Hisanori
Hayama, Mizuki
Matsuno, Hidetoshi
Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
title Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
title_full Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
title_fullStr Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
title_full_unstemmed Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
title_short Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
title_sort electrochemical friedel–crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443422/
https://www.ncbi.nlm.nih.gov/pubmed/36105724
http://dx.doi.org/10.3762/bjoc.18.105
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