4.5 Review

Sulfonyl Fluorides (SFs): More Than Click Reagents?

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 27-28, Pages 3648-3666

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800464

Keywords

Sulfonyl fluoride; Orthogonal reactions; Sulfur-fluoride exchange; Click chemistry; Fluorides; Synthesis design

Funding

  1. University of KwaZulu Natal (UKZN)
  2. South African National Research Foundation [87706]
  3. Department of Medicinal Chemistry, Uppsala University, Sweden

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Sulfonyl fluoride (SF) containing substances are currently attracting enormous attention among practitioners of both chemical biology and synthetic organic chemistry. The groups of Jones and Liskamp have demonstrated the potential of sulfonyl fluorides as selective covalent inhibitors in studies related to drug discovery and chemical biology, respectively, in the last few years. The Sharpless group has extended the repertoire of click-reactions to those involving sulfonyl fluorides, that is, sulfur-fluoride exchange (SuFEx), a development that quickly triggered the interest in this functional group in the community of synthetic organic chemists. In this microreview, we aim to give an account of the synthetic chemistry surrounding sulfonyl fluoride containing substances from a historical perspective to present day developments.

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