Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1,4-diazabicyclooctane Salts (Selectfluor Reagents)

Article abstract of DOI:10.1021/jo00062a023

The new "N-F"-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo<2.2.2>octane salts (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo<2.2.2>octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates.These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing α-H atoms, certain carbanions, and mildly activated aromatic compounds.The products were obtained with good yields and regioselectivity under very mild reaction conditions.