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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Detalles Bibliográficos
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
Descripción
Sumario: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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