Novel Approaches to Access Arylfluorosulfates and Sulfamoyl Fluorides Based on Sulfur (VI) Fluoride Exchange

Curr Protoc Chem Biol. 2019 Jun;11(2):e64. doi: 10.1002/cpch.64. Epub 2019 Feb 28.


Sulfur (VI) fluoride exchange (SuFEx) is a new family of click chemistry reactions that relies on readily available sulfuryl fluoride (SO2 F2 ) and ethenesulfonyl fluoride to build diverse chemical structures bearing the SVI -F motif, such as fluorosulfate (-OSO2 F) and sulfonyl fluoride (-SO2 F). These motifs could be useful functional groups and connective linkers in organic synthesis. This unit describes two protocols for performing SuFEx. The first protocol describes an in situ method for rapid generation of arylfluorosulfates in 96-well plates for high-throughput screening. The second protocol outlines use of a shelf-stable fluorosulfuryl imidazolium salt for generating arylfluorosulfates and sulfamoyl fluorides. © 2019 by John Wiley & Sons, Inc.

Keywords: SuFEx; arylfluorosulfate; azolium salts; click chemistry; sulfamoyl fluoride.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Click Chemistry
  • Fluorine / chemistry*
  • Molecular Structure
  • Sulfinic Acids / chemistry*
  • Sulfur / chemistry*
  • Sulfuric Acids / chemistry*


  • Sulfinic Acids
  • Sulfuric Acids
  • Fluorine
  • sulfuryl fluoride
  • Sulfur