Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane

A practical method for radical chain reduction of various aryl bromides and chlorides is introduced. The thermal process uses NaH and 1,4‐dioxane as reagents and 1,10‐phenanthroline as an initiator. Hydrodehalogenation can be combined with typical cyclization reactions, proving the nature of the rad...

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Autores principales: Hokamp, Tobias, Dewanji, Abhishek, Lübbesmeyer, Maximilian, Mück‐Lichtenfeld, Christian, Würthwein, Ernst‐Ulrich, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5698765/
https://www.ncbi.nlm.nih.gov/pubmed/28841248
http://dx.doi.org/10.1002/anie.201706534
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author Hokamp, Tobias
Dewanji, Abhishek
Lübbesmeyer, Maximilian
Mück‐Lichtenfeld, Christian
Würthwein, Ernst‐Ulrich
Studer, Armido
author_facet Hokamp, Tobias
Dewanji, Abhishek
Lübbesmeyer, Maximilian
Mück‐Lichtenfeld, Christian
Würthwein, Ernst‐Ulrich
Studer, Armido
author_sort Hokamp, Tobias
collection PubMed
description A practical method for radical chain reduction of various aryl bromides and chlorides is introduced. The thermal process uses NaH and 1,4‐dioxane as reagents and 1,10‐phenanthroline as an initiator. Hydrodehalogenation can be combined with typical cyclization reactions, proving the nature of the radical mechanism. These chain reactions proceed by electron catalysis. DFT calculations and mechanistic studies support the suggested mechanism.
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spelling pubmed-56987652017-11-30 Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane Hokamp, Tobias Dewanji, Abhishek Lübbesmeyer, Maximilian Mück‐Lichtenfeld, Christian Würthwein, Ernst‐Ulrich Studer, Armido Angew Chem Int Ed Engl Communications A practical method for radical chain reduction of various aryl bromides and chlorides is introduced. The thermal process uses NaH and 1,4‐dioxane as reagents and 1,10‐phenanthroline as an initiator. Hydrodehalogenation can be combined with typical cyclization reactions, proving the nature of the radical mechanism. These chain reactions proceed by electron catalysis. DFT calculations and mechanistic studies support the suggested mechanism. John Wiley and Sons Inc. 2017-09-19 2017-10-16 /pmc/articles/PMC5698765/ /pubmed/28841248 http://dx.doi.org/10.1002/anie.201706534 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://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
Hokamp, Tobias
Dewanji, Abhishek
Lübbesmeyer, Maximilian
Mück‐Lichtenfeld, Christian
Würthwein, Ernst‐Ulrich
Studer, Armido
Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
title Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
title_full Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
title_fullStr Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
title_full_unstemmed Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
title_short Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4‐Dioxane
title_sort radical hydrodehalogenation of aryl bromides and chlorides with sodium hydride and 1,4‐dioxane
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5698765/
https://www.ncbi.nlm.nih.gov/pubmed/28841248
http://dx.doi.org/10.1002/anie.201706534
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