Synfacts 2009(4): 0429-0429  
DOI: 10.1055/s-0028-1087834
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

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

Contributor(s): Paul Knochel, Andreas J. Wagner
H.-Q. Do, O. Daugulis*
University of Houston, USA
Further Information

Publication History

Publication Date:
23 March 2009 (online)


The in situ halogenation of acidic sp² 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.