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通过芳基卤化物的多功能π-扩展实现多环和七元环嵌入芳香族化合物的区域选择性合成。

Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides.

机构信息

Department of Applied Biology and Chemical Technology & SKLC, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, Hong Kong.

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, Hong Kong.

出版信息

Angew Chem Int Ed Engl. 2017 Jun 12;56(25):7166-7170. doi: 10.1002/anie.201703551. Epub 2017 May 16.

DOI:10.1002/anie.201703551
PMID:28510348
Abstract

A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C-H activator and ethylene synthon via a retro-Diels-Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.

摘要

发展了一种基于芳基卤化物、2-卤代芳基羧酸和降冰片二烯的三组分交叉偶联的多功能π-扩展反应。该转化由羧基的方向和随后的脱羧驱动，而降冰片二烯通过逆狄尔斯-阿尔德反应作为邻位 C-H 活化剂和乙烯合成子。进行了全面的 DFT 计算以解释催化中间体。

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