Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates

A synthetic protocol for the preparation of 5‐(aryl)dibenzothiophenium salts starting from inexpensive dibenzothiophene S‐oxide and simple arenes is reported. The scope of the method regarding the nature of the arene is evaluated, intermediates along the reaction sequence have been trapped, and side...

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Autores principales: Kafuta, Kevin, Korzun, André, Böhm, Marvin, Golz, Christopher, Alcarazo, Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7004049/
https://www.ncbi.nlm.nih.gov/pubmed/31680351
http://dx.doi.org/10.1002/anie.201912383
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author Kafuta, Kevin
Korzun, André
Böhm, Marvin
Golz, Christopher
Alcarazo, Manuel
author_facet Kafuta, Kevin
Korzun, André
Böhm, Marvin
Golz, Christopher
Alcarazo, Manuel
author_sort Kafuta, Kevin
collection PubMed
description A synthetic protocol for the preparation of 5‐(aryl)dibenzothiophenium salts starting from inexpensive dibenzothiophene S‐oxide and simple arenes is reported. The scope of the method regarding the nature of the arene is evaluated, intermediates along the reaction sequence have been trapped, and side‐reactions identified. In addition, the X‐ray structures of a complete set of these salts are reported and their reactivities studied. Specifically, chemoselective Suzuki coupling is observed at the dibenzothiophenium in the presence of iodides.
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spelling pubmed-70040492020-02-11 Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates Kafuta, Kevin Korzun, André Böhm, Marvin Golz, Christopher Alcarazo, Manuel Angew Chem Int Ed Engl Research Articles A synthetic protocol for the preparation of 5‐(aryl)dibenzothiophenium salts starting from inexpensive dibenzothiophene S‐oxide and simple arenes is reported. The scope of the method regarding the nature of the arene is evaluated, intermediates along the reaction sequence have been trapped, and side‐reactions identified. In addition, the X‐ray structures of a complete set of these salts are reported and their reactivities studied. Specifically, chemoselective Suzuki coupling is observed at the dibenzothiophenium in the presence of iodides. John Wiley and Sons Inc. 2019-11-26 2020-01-27 /pmc/articles/PMC7004049/ /pubmed/31680351 http://dx.doi.org/10.1002/anie.201912383 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Kafuta, Kevin
Korzun, André
Böhm, Marvin
Golz, Christopher
Alcarazo, Manuel
Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
title Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
title_full Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
title_fullStr Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
title_full_unstemmed Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
title_short Synthesis, Structure, and Reactivity of 5‐(Aryl)dibenzothiophenium Triflates
title_sort synthesis, structure, and reactivity of 5‐(aryl)dibenzothiophenium triflates
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7004049/
https://www.ncbi.nlm.nih.gov/pubmed/31680351
http://dx.doi.org/10.1002/anie.201912383
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