Photocatalytic conversion of aryl diazonium salts to sulfonyl fluorides

Cooper A. Vincent, Alexia Ripak, Ludovic Troian-Gautier, Uttam K. Tambar

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Sulfonyl fluorides have emerged as powerful tools in chemical biology for the selective labelling of proteins. A photocatalytic method is described for the conversion of aryl diazonium salts to aryl sulfonyl fluorides. The diazonium substrates are easily obtained in one step from functionalized anilines. We present the optimization of this mild method for the synthesis of sulfonyl fluorides, the scope of the transformation with a series of functionalized diazonium salts, and we discuss photophysical measurements that provide detailed information about the mechanism of the photochemical process.

Original languageEnglish (US)
Article number133364
JournalTetrahedron
Volume139
DOIs
StatePublished - Jun 12 2023

Keywords

  • Diazonium salts
  • Electron transfer
  • Photocatalyst
  • Sulfonyl fluorides

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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