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Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines

A novel and very simple to perform electrochemical approach for the synthesis of several N‐cyanosulfilimines in good to excellent yields was established. This method provides access to biologically relevant sulfoximines by consecutive oxidation using electro‐generated periodate. This route can be ea...

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Detalles Bibliográficos
Autores principales: Klein, Martin, Waldvogel, Siegfried R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597142/
https://www.ncbi.nlm.nih.gov/pubmed/34409715
http://dx.doi.org/10.1002/anie.202109033
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author Klein, Martin
Waldvogel, Siegfried R.
author_facet Klein, Martin
Waldvogel, Siegfried R.
author_sort Klein, Martin
collection PubMed
description A novel and very simple to perform electrochemical approach for the synthesis of several N‐cyanosulfilimines in good to excellent yields was established. This method provides access to biologically relevant sulfoximines by consecutive oxidation using electro‐generated periodate. This route can be easily scaled‐up to gram quantities. The S,N coupling is carried out at an inexpensive carbon anode by direct oxidation of sulfide. Therefore, the designed process is atom economic and represents a new “green route” for the synthesis of sulfilimines and sulfoximines.
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spelling pubmed-85971422021-11-22 Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines Klein, Martin Waldvogel, Siegfried R. Angew Chem Int Ed Engl Communications A novel and very simple to perform electrochemical approach for the synthesis of several N‐cyanosulfilimines in good to excellent yields was established. This method provides access to biologically relevant sulfoximines by consecutive oxidation using electro‐generated periodate. This route can be easily scaled‐up to gram quantities. The S,N coupling is carried out at an inexpensive carbon anode by direct oxidation of sulfide. Therefore, the designed process is atom economic and represents a new “green route” for the synthesis of sulfilimines and sulfoximines. John Wiley and Sons Inc. 2021-09-22 2021-10-18 /pmc/articles/PMC8597142/ /pubmed/34409715 http://dx.doi.org/10.1002/anie.202109033 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Klein, Martin
Waldvogel, Siegfried R.
Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines
title Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines
title_full Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines
title_fullStr Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines
title_full_unstemmed Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines
title_short Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines
title_sort anodic dehydrogenative cyanamidation of thioethers: simple and sustainable synthesis of n‐cyanosulfilimines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597142/
https://www.ncbi.nlm.nih.gov/pubmed/34409715
http://dx.doi.org/10.1002/anie.202109033
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