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肖尔反应:合成弯曲型多环芳烃的有力工具

The Scholl Reaction as a Powerful Tool for Synthesis of Curved Polycyclic Aromatics.

作者信息

Zhang Yiqun, Pun Sai Ho, Miao Qian

机构信息

Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.

出版信息

Chem Rev. 2022 Sep 28;122(18):14554-14593. doi: 10.1021/acs.chemrev.2c00186. Epub 2022 Aug 12.

Abstract

The past decade has witnessed remarkable success in the synthesis of curved polycyclic aromatics through Scholl reactions which enable oxidative aryl-aryl coupling even in company with the introduction of significant steric strain. These curved polycyclic aromatics are not only unique objects of structural organic chemistry in relation to the nature of aromaticity but also play an important role in bottom-up approaches to precise synthesis of nanocarbons of unique topology. Moreover, they have received considerable attention in the fields of supramolecular chemistry and organic functional materials because of their interesting properties and promising applications. Despite the great success of Scholl reactions in synthesis of curved polycyclic aromatics, the outcome of a newly designed substrate in the Scholl reaction still cannot be predicted in a generic and precise manner largely due to limited understanding on the reaction mechanism and possible rearrangement processes. This review provides an overview of Scholl reactions with a focus on their applications in synthesis of curved polycyclic aromatics with interesting structures and properties and aims to shed light on the key factors that affect Scholl reactions in synthesizing sterically strained polycyclic aromatics.

摘要

在过去十年中,通过肖尔反应合成弯曲型多环芳烃取得了显著成功,该反应即使在引入显著空间位阻的情况下也能实现氧化芳基-芳基偶联。这些弯曲型多环芳烃不仅是结构有机化学中与芳香性本质相关的独特研究对象,而且在自下而上精确合成具有独特拓扑结构的纳米碳的方法中发挥着重要作用。此外,由于其有趣的性质和潜在的应用,它们在超分子化学和有机功能材料领域受到了广泛关注。尽管肖尔反应在弯曲型多环芳烃的合成中取得了巨大成功,但由于对反应机理和可能的重排过程了解有限,新设计的底物在肖尔反应中的结果仍然无法以通用且精确的方式预测。本综述概述了肖尔反应,重点介绍了其在合成具有有趣结构和性质的弯曲型多环芳烃中的应用,旨在阐明在合成空间位阻多环芳烃时影响肖尔反应的关键因素。

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