Yasui Kosuke, Kamitani Miharu, Fujimoto Hayato, Tobisu Mamoru
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan.
Org Lett. 2021 Mar 5;23(5):1572-1576. doi: 10.1021/acs.orglett.0c04281. Epub 2021 Feb 12.
We report on the N-heterocyclic carbene (NHC)-catalyzed Truce-Smiles rearrangement of aniline derivatives, in which an unactivated C(aryl)-N bond is cleaved, leading to the formation of a new C(aryl)-C bond. The key to the success of this reaction is the utilization of a highly nucleophilic NHC, which enables the formation of a highly nucleophilic ylide intermediate that is generated from an α,β-unsaturated amide.
我们报道了N-杂环卡宾（NHC）催化的苯胺衍生物的Truce-Smiles重排反应，该反应中未活化的C（芳基）-N键发生断裂，从而形成新的C（芳基）-C键。该反应成功的关键在于使用了高亲核性的NHC，它能够促使由α,β-不饱和酰胺生成高亲核性的叶立德中间体。
