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Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)

Fluorinated group 16 moieties are attractive building blocks in synthetic chemistry but only few synthetic methods are available to prepare them. Herein, we report a new oxidative fluorination reagent capable of stabilizing reactive fluorinated anions. It consists of an SF(5) (−) anion and a chemica...

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Autores principales: Eder, Tobias, Buß, Florenz, Wilm, Lukas F. B., Seidl, Michael, Podewitz, Maren, Dielmann, Fabian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826459/
https://www.ncbi.nlm.nih.gov/pubmed/36018610
http://dx.doi.org/10.1002/anie.202209067
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author Eder, Tobias
Buß, Florenz
Wilm, Lukas F. B.
Seidl, Michael
Podewitz, Maren
Dielmann, Fabian
author_facet Eder, Tobias
Buß, Florenz
Wilm, Lukas F. B.
Seidl, Michael
Podewitz, Maren
Dielmann, Fabian
author_sort Eder, Tobias
collection PubMed
description Fluorinated group 16 moieties are attractive building blocks in synthetic chemistry but only few synthetic methods are available to prepare them. Herein, we report a new oxidative fluorination reagent capable of stabilizing reactive fluorinated anions. It consists of an SF(5) (−) anion and a chemically inert phosphonium cation and is exceptionally thermally stable. Accordingly, it was used to generate the SeF(5) (−) and TeF(5) (−) anions from the elemental chalcogens and to prepare the unknown tetrafluoro(phenyl)‐λ(5)‐selenate PhSeF(4) (−) and ‐tellurate PhTeF(4) (−) from the corresponding diphenyl dichalcogenides. In addition, we show that further derivatization of [PhTeF(4)](−) by oxidation to trans‐PhTeF(4)O(−) and subsequent alkylation gives access to a new class of trans‐(alkoxy)(phenyl)tetrafluoro‐λ(6)‐tellanes (trans‐PhTeF(4)OR), thus providing an approach to introduce the functional group into organic molecules.
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spelling pubmed-98264592023-01-09 Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6) Eder, Tobias Buß, Florenz Wilm, Lukas F. B. Seidl, Michael Podewitz, Maren Dielmann, Fabian Angew Chem Int Ed Engl Research Articles Fluorinated group 16 moieties are attractive building blocks in synthetic chemistry but only few synthetic methods are available to prepare them. Herein, we report a new oxidative fluorination reagent capable of stabilizing reactive fluorinated anions. It consists of an SF(5) (−) anion and a chemically inert phosphonium cation and is exceptionally thermally stable. Accordingly, it was used to generate the SeF(5) (−) and TeF(5) (−) anions from the elemental chalcogens and to prepare the unknown tetrafluoro(phenyl)‐λ(5)‐selenate PhSeF(4) (−) and ‐tellurate PhTeF(4) (−) from the corresponding diphenyl dichalcogenides. In addition, we show that further derivatization of [PhTeF(4)](−) by oxidation to trans‐PhTeF(4)O(−) and subsequent alkylation gives access to a new class of trans‐(alkoxy)(phenyl)tetrafluoro‐λ(6)‐tellanes (trans‐PhTeF(4)OR), thus providing an approach to introduce the functional group into organic molecules. John Wiley and Sons Inc. 2022-09-12 2022-10-17 /pmc/articles/PMC9826459/ /pubmed/36018610 http://dx.doi.org/10.1002/anie.202209067 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Eder, Tobias
Buß, Florenz
Wilm, Lukas F. B.
Seidl, Michael
Podewitz, Maren
Dielmann, Fabian
Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)
title Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)
title_full Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)
title_fullStr Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)
title_full_unstemmed Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)
title_short Oxidative Fluorination of Selenium and Tellurium Compounds using a Thermally Stable Phosphonium SF(5) (−) Salt Accessible from SF(6)
title_sort oxidative fluorination of selenium and tellurium compounds using a thermally stable phosphonium sf(5) (−) salt accessible from sf(6)
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826459/
https://www.ncbi.nlm.nih.gov/pubmed/36018610
http://dx.doi.org/10.1002/anie.202209067
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