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Tertiary‐Amine‐Initiated Synthesis of Acyl Fluorides from Carboxylic Acids and CF 3 SO 2 OCF 3
Author(s) -
Song HaiXia,
Tian ZeYu,
Xiao JiChang,
Zhang ChengPan
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003756
Subject(s) - reagent , chemistry , amine gas treating , trifluoromethanesulfonate , tertiary amine , organic chemistry , trifluoromethyl , functional group , carboxylic acid , reaction conditions , combinatorial chemistry , catalysis , alkyl , polymer
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.