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异氰与 -溴苯甲醛的反应差异:具有异吲哚啉酮核的酮亚胺和内酰胺的合成。

Divergent Reaction of Isocyanides with -Bromobenzaldehydes: Synthesis of Ketenimines and Lactams with Isoindolinone Cores.

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, People's Republic of China.

Analysis and Testing Center, Soochow University, Suzhou 215123, People's Republic of China.

出版信息

Org Lett. 2021 Oct 1;23(19):7342-7347. doi: 10.1021/acs.orglett.1c02422. Epub 2021 Sep 15.

Abstract

A divergent reaction of isocyanides with -bromobenzaldehydes for the synthesis of isoindolinone-derived ketenimines and lactams was disclosed. The reaction features readily available reactants, relatively mild conditions, and high yields of products. Ketenimines could be applied in further transformations for access to other functional molecules. A mechanism study showed that the palladium-migration/imine-insertion process was the key step in this reaction.

摘要

一种异氰化物与 -溴苯甲醛的发散反应,用于合成异吲哚啉酮衍生的酮烯亚胺和内酰胺。该反应具有原料易得、反应条件温和、产物收率高的特点。酮烯亚胺可以进一步转化为其他功能分子。机理研究表明,钯迁移/亚胺插入过程是该反应的关键步骤。

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