Lemmerer Miran, Maulide Nuno
Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Str. 38, 1090, Vienna, Austria.
Chemistry. 2023 Nov 24;29(66):e202302490. doi: 10.1002/chem.202302490. Epub 2023 Oct 24.
The combination of Lewis bases with α,β-unsaturated carbonyls allows the in-situ generation of enolates without the need for strong Brønsted bases. Recently developed synthetic methods employ this approach for arylation followed by elimination of the Lewis base, regenerating the alkene. This strategy has been deployed for formal α- or β-C-H arylation in different contexts, namely (a) transition metal catalysis, (b) rearrangement reactions utilizing hypervalent main group elements and (c) organocatalysis. This concept article provides an overview of the developed strategies, highlighting and contextualizing their features.
路易斯碱与α,β-不饱和羰基化合物的结合使得烯醇盐能够原位生成,而无需使用强碱。最近开发的合成方法采用这种方法进行芳基化反应,随后消除路易斯碱,使烯烃再生。该策略已在不同背景下用于形式上的α-或β-C-H芳基化反应,即(a)过渡金属催化、(b)利用高价主族元素的重排反应和(c)有机催化。这篇概念文章概述了已开发的策略,突出并阐述了它们的特点。