Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap sta...

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Detalles Bibliográficos
Autores principales: Spils, Julian, Wirth, Thomas, Nachtsheim, Boris J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9830492/
https://www.ncbi.nlm.nih.gov/pubmed/36686040
http://dx.doi.org/10.3762/bjoc.19.2
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author Spils, Julian
Wirth, Thomas
Nachtsheim, Boris J
author_facet Spils, Julian
Wirth, Thomas
Nachtsheim, Boris J
author_sort Spils, Julian
collection PubMed
description We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap starting materials. An acid-catalyzed Friedel–Crafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield.
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spelling pubmed-98304922023-01-20 Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation Spils, Julian Wirth, Thomas Nachtsheim, Boris J Beilstein J Org Chem Letter We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap starting materials. An acid-catalyzed Friedel–Crafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield. Beilstein-Institut 2023-01-03 /pmc/articles/PMC9830492/ /pubmed/36686040 http://dx.doi.org/10.3762/bjoc.19.2 Text en Copyright © 2023, Spils 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
Spils, Julian
Wirth, Thomas
Nachtsheim, Boris J
Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
title Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
title_full Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
title_fullStr Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
title_full_unstemmed Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
title_short Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
title_sort two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9830492/
https://www.ncbi.nlm.nih.gov/pubmed/36686040
http://dx.doi.org/10.3762/bjoc.19.2
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