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Issue 8, 2018
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Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

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Abstract

Proline-based designer surfactant FI-750-M has been demonstrated to enable selective nucleophilic aromatic substitution of polyfluoro(hetero)arenes by sulfinate salts in water under mild micellar conditions. Resultant sulfones were obtained from diverse substrates in good yields without side product formation and could usually be purified by simple filtration. The nature of micelles of FI-750-M and the solubility of coupling partners in different micellar regions has been supported by dynamic light scattering, cryo-TEM, and DFT calculations.

Graphical abstract: Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

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Publication details

The article was received on 22 Nov 2017, accepted on 13 Mar 2018 and first published on 13 Mar 2018


Article type: Paper
DOI: 10.1039/C7GC03514D
Citation: Green Chem., 2018,20, 1784-1790
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    Micelle-enabled clean and selective sulfonylation of polyfluoroarenes in water under mild conditions

    J. D. Smith, T. N. Ansari, M. P. Andersson, D. Yadagiri, F. Ibrahim, S. Liang, G. B. Hammond, F. Gallou and S. Handa, Green Chem., 2018, 20, 1784
    DOI: 10.1039/C7GC03514D

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