Hydrodehalogenation of Haloarenes by a Sodium Hydride-Iodide Composite

Derek Yiren Ong; Ciputra Tejo; Kai Xu; Hajime Hirao; Shunsuke Chiba

doi:10.1002/anie.201611495

Hydrodehalogenation of Haloarenes by a Sodium Hydride-Iodide Composite

Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1840-1844. doi: 10.1002/anie.201611495. Epub 2017 Jan 10.

Authors

Derek Yiren Ong¹, Ciputra Tejo¹, Kai Xu¹, Hajime Hirao¹, Shunsuke Chiba¹

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.

PMID: 28071853
DOI: 10.1002/anie.201611495

Abstract

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.

Keywords: DFT calculations; haloarenes; hydrodehalogenation; reduction; sodium hydride.

Publication types

Research Support, Non-U.S. Gov't