Concise synthesis of succinimide-fused 1,3-cyclohexadienes via Co-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes and maleimides

Kaili Cen; Ziyi Zhai; Yuan Liu; Jiahao Wei; Mixia Ouyang; Guojun He; Shuyu Huang; Feng Zhao; Jinhui Cai

doi:10.1039/D4QO00435C

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Concise synthesis of succinimide-fused 1,3-cyclohexadienes via Co-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes and maleimides†

Kaili Cen,‡^a Ziyi Zhai,‡^a Yuan Liu,‡^c Jiahao Wei,^d Mixia Ouyang,^a Guojun He,^a Shuyu Huang,^a Feng Zhao

*^b and Jinhui Cai

*^a

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, Hunan, China
E-mail: jinhuicai@usc.edu.cn

^b Hunan Provincial Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, Hunan, China
E-mail: zhaofenghnmu@163.com

^c Chuanshan College University of South China, University of China, Henyang 421001, Hunan, China

^d School of Pharmaceutical Science, University of South China, Henyang 421001, Hunan, China

Abstract

Herein, we report a new route towards succinimide-fused 1,3-cyclohexadienes through the reaction of 1,6-diynes with electron-deficient alkenes under cobalt catalysis. This method showed high efficiency, a wide substrate scope, good functional group tolerance, good atom economy, and easy scale-up. Furthermore, the succinimide-fused 1,3-cyclohexadienes were easily converted, via dehydrogenation under the cooperative work of iodine/CH₃ONa, in good to excellent yields to 7,9,11-triaryl-8H-acenaphtho[1,2-f]isoindole-8,10(9H)-dione derivatives, compounds expected to display good photophysical properties.

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DOI: https://doi.org/10.1039/D4QO00435C
Article type: Research Article
Submitted: 07 Mar 2024
Accepted: 16 Apr 2024
First published: 16 Apr 2024

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Org. Chem. Front., 2024,11, 3257-3262

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Concise synthesis of succinimide-fused 1,3-cyclohexadienes via Co-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes and maleimides

K. Cen, Z. Zhai, Y. Liu, J. Wei, M. Ouyang, G. He, S. Huang, F. Zhao and J. Cai, Org. Chem. Front., 2024, 11, 3257 DOI: 10.1039/D4QO00435C

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Organic Chemistry Frontiers

Concise synthesis of succinimide-fused 1,3-cyclohexadienes via Co-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes and maleimides†

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Concise synthesis of succinimide-fused 1,3-cyclohexadienes via Co-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes and maleimides

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