Tertiary-Amine-Initiated Synthesis of Acyl Fluorides from Carboxylic Acids and CF SO OCF.

Chemistry

School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, P. R. China.

Published: December 2020

AI Article Synopsis

  • A new method for deoxyfluorination of carboxylic acids using CF3SO2OCF has been developed, allowing for easy access to acyl fluorides at room temperature.
  • The technique is efficient and straightforward, with good results across a variety of substrates and functional groups, and uses environmentally friendly reagents.
  • This work marks the first time trifluoromethyl trifluoromethanesulfonate has been used as a fluorination reagent.

Article Abstract

A convenient method for deoxyfluorination of aromatic and aliphatic carboxylic acids with CF SO OCF 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 SO OCF 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.

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Source
http://dx.doi.org/10.1002/chem.202003756DOI Listing

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