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

Hai‐Xia Song, Zeyu Tian, Ji‐Chang Xiao, Cheng‐Pan Zhang

2020Chemistry - A European Journal36 citationsDOI

Abstract

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.

Topics & Concepts

Amine gas treatingTertiary amineChemistryCarboxylic acidMedicinal chemistryStereochemistryOrganic chemistryFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsChemical Synthesis and Analysis
Tertiary‐Amine‐Initiated Synthesis of Acyl Fluorides from Carboxylic Acids and CF<sub>3</sub>SO<sub>2</sub>OCF<sub>3</sub> | Litcius