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

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.