Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite

A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process. A simple protocol for...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-02, Vol.56 (7), p.1840-1844
Main Authors: Ong, Derek Yiren, Tejo, Ciputra, Xu, Kai, Hirao, Hajime, Chiba, Shunsuke
Format: Article
Language:English
Subjects:
Aromatic compounds
DFT calculations
haloarenes
hydrodehalogenation
Iodides
Lithium
reduction
Sodium
sodium hydride
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Summary:A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process. A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies show that an unusual concerted nucleophilic aromatic substitution operates in the present process.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201611495