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

Derek Yiren Ong, Ciputra Tejo, Kai Xu, Hajime Hirao^*, Shunsuke Chiba^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

87 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1840-1844
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	7
DOIs	https://doi.org/10.1002/anie.201611495
Publication status	Published - 6 Feb 2017
Externally published	Yes

Research Keywords

DFT calculations
haloarenes
hydrodehalogenation
reduction
sodium hydride

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10.1002/anie.201611495

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title = "Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite",

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",

author = "Ong, {Derek Yiren} and Ciputra Tejo and Kai Xu and Hajime Hirao and Shunsuke Chiba",

year = "2017",

month = feb,

day = "6",

doi = "10.1002/anie.201611495",

language = "English",

volume = "56",

pages = "1840--1844",

journal = "Angewandte Chemie - International Edition",

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T1 - Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite

AU - Ong, Derek Yiren

AU - Tejo, Ciputra

AU - Xu, Kai

AU - Hirao, Hajime

AU - Chiba, Shunsuke

PY - 2017/2/6

Y1 - 2017/2/6

N2 - 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.

AB - 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.

KW - DFT calculations

KW - haloarenes

KW - hydrodehalogenation

KW - reduction

KW - sodium hydride

UR - http://www.scopus.com/inward/record.url?scp=85010886912&partnerID=8YFLogxK

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U2 - 10.1002/anie.201611495

DO - 10.1002/anie.201611495

M3 - RGC 21 - Publication in refereed journal

SN - 1433-7851

VL - 56

SP - 1840

EP - 1844

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite

Abstract

Research Keywords

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