Zhou Rong, Liu Rongfang, Zhang Kai, Han Ling, Zhang Honghui, Gao Wenchao, Li Ruifeng
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, 030024, P. R. China.
Chem Commun (Camb). 2017 Jun 22;53(51):6860-6863. doi: 10.1039/c7cc03765a.
A novel P(NMe)-mediated formal carbon-halogen bond insertion of isatins into allylic and benzylic bromides/chlorides has been realized, leading to a facile synthesis of 3-halo 3,3'-disubstituted oxindoles. This reaction relies on the unique dual nucleophilic-electrophilic reactivity pattern of the Kukhtin-Ramirez adduct via a cascade S2-S2 process. It also represents a rare metal-free approach for carbon-halogen bond insertion. Upon treatment with trifluoroacetic acid, spirooxindole-γ-butyrolactones have been efficiently prepared from the corresponding insertion products.
实现了一种新型的由P(NMe)介导的异吲哚酮与烯丙基和苄基溴化物/氯化物的形式碳-卤键插入反应，从而简便地合成了3-卤代3,3'-二取代氧化吲哚。该反应通过级联S2-S2过程依赖于Kukhtin-Ramirez加合物独特的双亲核-亲电反应模式。它还代表了一种罕见的无金属碳-卤键插入方法。用三氟乙酸处理后，已从相应的插入产物高效制备了螺环氧化吲哚-γ-丁内酯。
