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. 2019 Apr 24;141(16):6499-6503.
doi: 10.1021/jacs.9b02436. Epub 2019 Apr 16.

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

Misuzu Nakajima  1 , Kazunori Miyamoto  1 , Keiichi Hirano  1 , Masanobu Uchiyama  1   2   3
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Diaryl-λ3-chloranes: Versatile Synthesis and Unique Reactivity as Aryl Cation Equivalent

Misuzu Nakajima et al. J Am Chem Soc. .

Abstract

We have developed a versatile, high-yield synthesis of diarylchloroniums/λ3-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/λ3-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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