Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 40, Issue 14, Pages 1687-1692Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202200112
Keywords
Electrochemicstry; Fluorides; Click chemistry; Sulfinic salt; Dehydrogenation
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Funding
- National Natural Science Foundation of China [21790332, 22071105, 22031008]
- QingLan Project of Jiangsu Education Department
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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.
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.
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