Issue 8, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Nov 2017
Accepted
13 Mar 2018
First published
13 Mar 2018

Green Chem., 2018,20, 1784-1790

Author version available

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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