New Pentafluorosulfanyls

  • Author: Veronika Belusa
  • Published Date: 10 November 2014
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: New Pentafluorosulfanyls

The pentafluorosulfanyl (SF5) group is important for the development of new materials, pharmaceuticals, and agrochemicals.

William R. Dolbier, Jr. and Oleksandr S. Kanishchev, University of Florida, Gainesville, USA, have synthesized a series of new substituted 2-pyridylsulfur pentafluorides, a moderately expensive and highly efficient chlorine-fluorine exchange reagent.
Excess oxidative fluorination of 2,2’-dipyridyl disulfides with a KF/Cl2/MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides. These molecules were found to undergo further chlorine–fluorine exchange reactions with silver(I) fluoride. This enables ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides.

This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.


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