Electrochemical Synthesis of Sulfonyl Fluorides with Triethylamine Hydrofluoride

Comprehensive Summary Hydrofluoride is an industry-preferred fluoride source, and finds extensively application to manufacture diverse fluoro chemicals. The Et3N-3HF complex is a liquid HF with improve safety. In this work, we report electrochemical synthesis of a series of sulfonyl fluoride with Et3N-3HF as fluoride source. The sulfinic salt is a smell-less, non-volatile, and air-stable sulfur source in this reaction. With the combination of Et3N-3HF and aryl/alkyl sulfinic salt, the sulfonyl fluorides are achieved without the use of external oxidant. In addition, we demonstrate further advantage in a tandem reaction involving Pd-catalyzed C-S cross-coupling and formation of S-F bond. A variety of functional groups including amino acids, heterocycles, halides are well tolerated.

Automated summary

In this work, the electrochemical synthesis of sulfonyl fluorides using Et3N-3HF as the fluoride source is reported. The reaction allows efficient synthesis of sulfonyl fluorides without the use of external oxidant by combining Et3N-3HF with aryl/alkyl sulfinic salt. Furthermore, the method demonstrates its advantage in a tandem reaction involving Pd-catalyzed C-S cross-coupling and formation of S-F bond, with good tolerance towards a variety of functional groups.