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Issue 12, 2019
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Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

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Abstract

The reaction of a metal complex containing a polar Fe–Mg bond with 2-(pentafluorophenyl)pyridine leads to selective C–F bond activation. A stepwise SNAr mechanism involving attack of the bimetallic nucleophile on the electron-deficient aromatic ring has been identified by DFT calculations. Despite the long and rich history of metal anions in organic synthesis, this is the first time the SNAr mechanism has been elucidated in detail for metal-based nucleophiles.

Graphical abstract: Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

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Article information


Submitted
06 Dec 2018
Accepted
14 Jan 2019
First published
14 Jan 2019

Chem. Commun., 2019,55, 1805-1808
Article type
Communication

Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

M. Garçon, C. Bakewell, A. J. P. White and M. R. Crimmin, Chem. Commun., 2019, 55, 1805
DOI: 10.1039/C8CC09701A

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