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通过C(sp) -H和C(sp) -H键活化实现配体促进的芳香酸与马来酰亚胺的[3+2]环化反应

Ligand-Enabled [3+2] Annulation of Aromatic Acids with Maleimides by C(sp )-H and C(sp )-H Bond Activation.

作者信息

Naskar Gouranga, Jeganmohan Masilamani

机构信息

Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, Tamil Nadu, India.

出版信息

Chemistry. 2022 Jul 11;28(39):e202200778. doi: 10.1002/chem.202200778. Epub 2022 May 26.

Abstract

A palladium-catalyzed [3+2] annulation of substituted benzoic acids with maleimides leading to tricyclic heterocyclic molecules having a free carboxylic group in a high atom- and step-economical manner is described. The reaction proceeds via a dual C-H bond activation such as C(sp )-H at the benzylic position and C(sp )-H bond activation at the meta position of substituted aromatics. An external ligand (MPAA) is crucial for the success of present protocol. Further, the decarboxylation and esterification of the free carboxylic acid group of observed products were carried out.

摘要

描述了钯催化取代苯甲酸与马来酰亚胺的[3+2]环化反应,该反应以高原子经济性和步骤经济性的方式生成具有游离羧基的三环杂环分子。该反应通过双重C-H键活化进行,例如苄基位置的C(sp) -H键活化和取代芳烃间位的C(sp) -H键活化。外部配体(MPAA)对于本反应方案的成功至关重要。此外,还对观察到的产物的游离羧酸基团进行了脱羧和酯化反应。

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