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二芳基-λ-氯代烷:作为芳基碳正离子等价物的多功能合成与独特反应性。

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

机构信息

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

Cluster of Pioneering Research (CPR), Advanced Elements Chemistry Laboratory, RIKEN , 2-1 Hirosawa , Wako-shi , Saitama 351-0198 , Japan.

出版信息

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

DOI:10.1021/jacs.9b02436
PMID:30969759
Abstract

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.

摘要

我们开发了一种通过温和条件下各种氯代芳烃与 readily prepared mesityldiazonium tetrakis(pentafluorophenyl)borate 反应制备二芳基氯𬭩/λ-氯仿的通用、高产合成方法。该反应的范围很广,包括 ArCl、ArBr 和 ArI。这里制备的二芳基氯𬭩/λ-氯仿在各个方面表现出独特的反应性,能够实现弱亲核试剂的分子间亲电芳基化反应和氯仿-卤仿交换反应。

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