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邻位乙烯基溴代苯与芳基溴的串联交叉偶联/环化反应合成多环芳烃化合物。

Sequential Cross-Coupling/Annulation of ortho-Vinyl Bromobenzenes with Aromatic Bromides for the Synthesis of Polycyclic Aromatic Compounds.

机构信息

The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China.

Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China.

出版信息

Angew Chem Int Ed Engl. 2019 Nov 11;58(46):16543-16547. doi: 10.1002/anie.201910792. Epub 2019 Sep 30.

Abstract

A sequential cross-coupling/annulation of ortho-vinyl bromobenzenes with aromatic bromides was realized, providing a direct and modular approach to access polycyclic aromatic compounds. A vinyl-coordinated palladacycle was proposed as the key intermediate for this sequential process. Excellent chemoselectivity and regioselectivity were observed in this transformation. The practicability of this method is highlighted by its broad substrate scope, excellent functional group tolerance, and rich transformations associated with the obtained products.

摘要

邻位取代溴代苯乙烯与芳基溴化物的串联交叉偶联/环化反应得到了实现,为多环芳烃化合物的构建提供了一种直接的、模块化的方法。一个乙烯基配位的钯环配合物被认为是这个串联反应的关键中间体。在这个转化中观察到了极好的化学选择性和区域选择性。该方法具有广泛的底物范围、优异的官能团耐受性以及与获得的产物相关的丰富转化,突出了其实用性。

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