Tertiary‐Amine‐Initiated Synthesis of Acyl Fluorides from Carboxylic Acids and CF 3 SO 2 OCF 3

Abstract A convenient method for deoxyfluorination of aromatic and aliphatic carboxylic acids with CF 3 SO 2 OCF 3 in the presence of a suitable base at room temperature has been developed. The reaction allows a straightforward access to a variety of acyl fluorides and proves that CF 3 SO 2 OCF 3 is...

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Published inChemistry : a European journal Vol. 26; no. 69; pp. 16261 - 16265
Main Authors Song, Hai‐Xia, Tian, Ze‐Yu, Xiao, Ji‐Chang, Zhang, Cheng‐Pan
Format Journal Article
LanguageEnglish
Published 09.12.2020
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Summary:Abstract A convenient method for deoxyfluorination of aromatic and aliphatic carboxylic acids with CF 3 SO 2 OCF 3 in the presence of a suitable base at room temperature has been developed. The reaction allows a straightforward access to a variety of acyl fluorides and proves that CF 3 SO 2 OCF 3 is an effective deoxyfluorination reagent for carboxylic acids. The method features simplicity, expeditiousness, high efficiency, ease of handling, good functional group tolerance, a wide range of substrates, excellent yields of products, compatibility of many amine initiators, use of environmentally friendly reagents, and effortless removal of byproducts. This reaction represents the first utilization of trifluoromethyl trifluoromethanesulfonate as a fluorination reagent.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202003756