Base-Mediated Halogenation of Acidic Aryl C-H Bonds at Higher Temperatures

Significance

The in situ halogenation of acidic sp^² carbon-hydrogen bonds in electron-deficient arenes and hetarenes is carried out in a novel approach generating a reactive organometallic intermediate in the presence of a halonium source. Both selective monohalogenation and exhaustive perhalogenation of multiple acidic C-H bonds are permitted by this procedure. Depending on the substrate, the reaction proceeds in moderate to excellent yields.