Electrochemical Synthesis of S-Aryl Dibenzothiophenium Triflates as Precursors for Selective Nucleophilic Aromatic (Radio)fluorination

A novel electrosynthetic approach to aryl dibenzothiophenium salts, including the direct intramolecular formation of a C-S bond in a metal-free, electrochemical key step under ambient conditions, is reported. The broad applicability of this method is demonstrated with 14 examples, including nitrogen-containing heterocycles in isolated yields up to 72%. The resulting sulfonium salts can be used as precursors for fluorine labeling to give [F-18]fluoroarenes as found in PET tracer ligands.

Automated summary

A novel electrosynthetic approach for the synthesis of aryl dibenzothiophenium salts, including the metal-free, electrochemical formation of a C-S bond under ambient conditions, has been reported. The broad applicability of this method has been demonstrated with 14 examples, achieving isolated yields of up to 72%, including nitrogen-containing heterocycles. The resulting sulfonium salts can serve as precursors for the synthesis of [F-18]fluoroarenes found in PET tracer ligands.