Evano Gwilherm, Theunissen Cédric
Laboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université libre de Bruxelles (ULB), Avenue F.D. Roosevelt 50, CP160/06, 1050, Brussels, Belgium.
Angew Chem Int Ed Engl. 2019 May 27;58(22):7202-7236. doi: 10.1002/anie.201806629. Epub 2019 Feb 14.
Alkylation of arenes is one of the most fundamental transformations in chemical synthesis and leads to privileged scaffolds in many areas of science. Classical methods for the introduction of alkyl groups to arenes are mostly based on the Friedel-Crafts reaction, radical additions, metalation, or prefunctionalization of the arene: these methods, however, suffer from limitations in scope, efficiency, and selectivity. Moreover, they are based on the innate reactivity of the starting arene, favoring the alkylation at a certain position and rendering the introduction of alkyl chains at other positions much more challenging. This can be addressed by the use of a directing group that facilitates, in the presence of a metal catalyst, the regioselective alkylation of a C-H bond. These directed alkylations of C-H bonds in arenes will be comprehensively summarized in this Review.
芳烃的烷基化是化学合成中最基本的转化反应之一，并在许多科学领域中产生了重要的骨架结构。将烷基引入芳烃的经典方法主要基于傅克反应、自由基加成、金属化或芳烃的预官能团化：然而，这些方法在适用范围、效率和选择性方面存在局限性。此外，它们基于起始芳烃的固有反应性，有利于在特定位置进行烷基化，而在其他位置引入烷基链则更具挑战性。这可以通过使用导向基团来解决，该导向基团在金属催化剂存在下促进C-H键的区域选择性烷基化。本文将对芳烃中C-H键的这些导向烷基化反应进行全面总结。
