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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 and Studer, Armido 2017. Radical hydrodehalogenation of aryl bromides and chlorides with sodium hydride and 1,4-Dioxane. Angewandte Chemie - International Edition 56 (43) , pp. 13275-13278. 10.1002/anie.201706534

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Abstract

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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley-Blackwell
ISSN: 1433-7851
Date of First Compliant Deposit: 12 June 2018
Date of Acceptance: 25 August 2017
Last Modified: 13 Jun 2018 12:15
URI: http://orca.cf.ac.uk/id/eprint/112222

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