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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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Publication details

The article was received on 06 Dec 2018, accepted on 14 Jan 2019 and first published on 14 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC09701A
Chem. Commun., 2019,55, 1805-1808

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    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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