Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2008-2016. doi: 10.6023/cjoc201804007 shu

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

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

Corresponding author: Tang Yu, tytang@jnu.edu.cn Zhang Yuanming, tzhangym@jnu.edu.cn
Received Date: 4 April 2018
Revised Date: 2 May 2018
Available Online: 17 August 2018
Fund Project: 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)the National Natural Science Foundation of China 21274083the National University Student Innovation and Entrepreneurship Training Program of China 82617055

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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.
- isoindole,
- Barbier-Grignard reaction,
- Ta₂O₅,
- oxidative coupling
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