Synthesis and reactivity of azole-based iodazinium salts

A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic protocol that allowed us to synthesize these novel cyclic iodonium salts in their mono- and dicationic forms, we gained in-depth structural information through single-crystal analysis and dem...

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Autores principales: Kuczmera, Thomas J, Dietz, Annalena, Boelke, Andreas, Nachtsheim, Boris J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028571/
https://www.ncbi.nlm.nih.gov/pubmed/36960303
http://dx.doi.org/10.3762/bjoc.19.27
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author Kuczmera, Thomas J
Dietz, Annalena
Boelke, Andreas
Nachtsheim, Boris J
author_facet Kuczmera, Thomas J
Dietz, Annalena
Boelke, Andreas
Nachtsheim, Boris J
author_sort Kuczmera, Thomas J
collection PubMed
description A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic protocol that allowed us to synthesize these novel cyclic iodonium salts in their mono- and dicationic forms, we gained in-depth structural information through single-crystal analysis and demonstrated the ring opening of the heterocycle-bridged iodonium species. For an exclusive set of dicationic imidazoiodaziniums, we show highly delicate post-oxidation functionalizations retaining the hypervalent iodine center.
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spelling pubmed-100285712023-03-22 Synthesis and reactivity of azole-based iodazinium salts Kuczmera, Thomas J Dietz, Annalena Boelke, Andreas Nachtsheim, Boris J Beilstein J Org Chem Full Research Paper A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic protocol that allowed us to synthesize these novel cyclic iodonium salts in their mono- and dicationic forms, we gained in-depth structural information through single-crystal analysis and demonstrated the ring opening of the heterocycle-bridged iodonium species. For an exclusive set of dicationic imidazoiodaziniums, we show highly delicate post-oxidation functionalizations retaining the hypervalent iodine center. Beilstein-Institut 2023-03-16 /pmc/articles/PMC10028571/ /pubmed/36960303 http://dx.doi.org/10.3762/bjoc.19.27 Text en Copyright © 2023, Kuczmera 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
Kuczmera, Thomas J
Dietz, Annalena
Boelke, Andreas
Nachtsheim, Boris J
Synthesis and reactivity of azole-based iodazinium salts
title Synthesis and reactivity of azole-based iodazinium salts
title_full Synthesis and reactivity of azole-based iodazinium salts
title_fullStr Synthesis and reactivity of azole-based iodazinium salts
title_full_unstemmed Synthesis and reactivity of azole-based iodazinium salts
title_short Synthesis and reactivity of azole-based iodazinium salts
title_sort synthesis and reactivity of azole-based iodazinium salts
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028571/
https://www.ncbi.nlm.nih.gov/pubmed/36960303
http://dx.doi.org/10.3762/bjoc.19.27
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