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Issue 54, 2017
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SNAr catalysis enhanced by an aromatic donor–acceptor interaction; facile access to chlorinated polyfluoroarenes

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Abstract

Selective catalytic SNAr reaction of polyfluoroaryl C–F bonds with chloride is shown. Stoichiometric TMSCl makes the reaction exergonic and allows catalysis, which involves ground state elevation of chloride, aromatic donor–acceptor interactions, and stabilization of the Meisenheimer complex. Traditional cross-coupling of the products is now possible and demonstrates the utility.

Graphical abstract: SNAr catalysis enhanced by an aromatic donor–acceptor interaction; facile access to chlorinated polyfluoroarenes

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Publication details

The article was received on 25 May 2017, accepted on 14 Jun 2017 and first published on 21 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC03996D
Citation: Chem. Commun., 2017,53, 7545-7548
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    SNAr catalysis enhanced by an aromatic donor–acceptor interaction; facile access to chlorinated polyfluoroarenes

    S. Senaweera and J. D. Weaver, Chem. Commun., 2017, 53, 7545
    DOI: 10.1039/C7CC03996D

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