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

J Am Chem Soc

Graduate School of Pharmaceutical Sciences , The University of Tokyo, 7-3-1 Hongo , Bunkyo-ku, Tokyo 113-0033 , Japan.

Published: April 2019

We have developed a versatile, high-yield synthesis of diarylchloroniums/λ-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/λ-chloranes prepared here show unique reactivity in various respects, enabling intermolecular electrophilic arylation reaction of weak nucleophiles, and chlorane-halogane exchange reaction.

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http://dx.doi.org/10.1021/jacs.9b02436DOI Listing

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