Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction

doi:10.6023/cjoc201804007

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 2008-2016.DOI: 10.6023/cjoc201804007 Previous Articles Next Articles

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通过Barbier-Grignard型反应合成1,3-二芳基或二烷基-2H-异吲哚-4,7-二酮

刘宏, 董慧茹, 安锐, 唐渝, 许开天, 张渊明

暨南大学化学与材料学院化学系广州 510632

收稿日期:2018-04-04 修回日期:2018-05-02 发布日期:2018-05-17
通讯作者: 唐渝, 张渊明 E-mail:tytang@jnu.edu.cn;tzhangym@jnu.edu.cn
基金资助:
国家自然科学基金（No.21274083）、全国大学生创新创业培养计划（No.82617055）资助项目.

Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction

Liu Hong, Dong Huiru, An Rui, Tang Yu, Xu Kaitian, Zhang Yuanming

Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632

Received:2018-04-04 Revised:2018-05-02 Published:2018-05-17
Contact: 10.6023/cjoc201804007 E-mail:tytang@jnu.edu.cn;tzhangym@jnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21274083) and the National University Student Innovation and Entrepreneurship Training Program of China (No. 82617055).

1. Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction.PDF(3287KB)

Abstract

A novel, convenient and efficient protocol to N-heterocyclic derivatives of 1,3-diaryl or diaklyl-2H-isoin-dole-4,7-dione has been developed via the Barbier-Grignard-type reaction. Good to excellent yields up to 96% have been achieved by performing the reaction in one pot using Ta₂O₅ as the catalyst. The protocol displays good tolerance to different aryl and alkyl bromides. Based on some experimental results, a plausible mechanism involving nucleophilic addition and electron transfer has been proposed. The quinone structure in 1,3-diphenyl-2H-isoindole-4,7-dione (3a) makes it coupling with amine to form more complicated structure.

Key words: isoindole, Barbier-Grignard reaction, Ta₂O₅, oxidative coupling

Cite this article

Liu Hong, Dong Huiru, An Rui, Tang Yu, Xu Kaitian, Zhang Yuanming. Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction[J]. Chin. J. Org. Chem., 2018, 38(8): 2008-2016.

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通过Barbier-Grignard型反应合成1,3-二芳基或二烷基-2H-异吲哚-4,7-二酮

Synthesis of 1,3-Diaryl or Dialkyl-2H-isoindole-4,7-dione via Barbier-Grignard-Type Reaction

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