Diaryl-λ3-chloranes: Versatile Synthesis and Unique Reactivity as Aryl Cation Equivalent

We have developed a versatile, high-yield synthesis of diarylchloroniums/lambda(3)-chloranes through the reaction of various chloroarenes with readily prepared mesityldiazonium tetrakis(pentafluorophenyl)borate under mild conditions. The scope of the reaction is broad, including ArCl, ArBr, and ArI. The diarylchloroniums/lambda(3)-chloranes prepared here show unique reactivity in various respects, enabling intermolecular electrophilic arylation reaction of weak nucleophiles, and chlorane-halogane exchange reaction.