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Chinese Journal of Organic Chemistry    

ARTICLE

氮杂环卡宾（NHC）和1,2-环丁烯二酮协同参与的开环重建反应

王晓梅a†, 李运涛a†, 李师伍a, 李少川b*, 赵志飞a*   

  1. a石河子大学化学化工学院/化工绿色过程省部共建国家重点实验室培育基地 新疆石河子 832000;
    b绿色碳化学安徽省重点实验室,阜阳师范大学化学与材料工程学院,安徽省阜阳市,236037,中国
  • 收稿日期:2026-06-03 修回日期:2026-07-13
  • 作者简介:†共同第一作者
  • 基金资助:
    新疆维吾尔自治区“天池英才”青年博士项目、国家自然科学基金项目(C类,22501050)、安徽省教育厅项目 (2024AH051457)、阜阳师范大学科研启动经费 (2023KYQD0021)、阜阳师范大学校级人才项目 (rcxm202502)和化学类产学研合作项目 (HX2025146000).

Cooperative Ring-Opening Reconstruction Reaction of N-Heterocyclic Carbenes with 1,2-Cyclobutenedione

Wang Xiaomeia†, Li Yuntaoa†, Li Shiwua, Li Shaochuanb,*, Zhao Zhifeia,*   

  1. a School School of Chemistry and Chemical Engineering, Shihezi University/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering Shihezi, Xinjiang 832000;
    b Anhui Provincial Key Laboratory of Green Carbon Chemistry, School of Chemistry & Materials Engineering, Fuyang Normal University, Fuyang, 236037, PR China
  • Received:2026-06-03 Revised:2026-07-13
  • Contact: *E-mail: zhaozf@shzu.edu.cn, 202305004@fynu.edu.cn.
  • About author:†The authors contributed equally to this work.
  • Supported by:
    Tianchi Talent Project of Xinjiang Uygur Autonomous Region, National Natural Science Foundation of Chian (22501050), Anhui Provincial Department of Education Project (2024AH051457), Start-up funds from Fuyang Normal University (2023KYQD0021), University-Level Talent project from Fuyang Normal University (rcxm202502) and Chemistry industry-university-research project (HX2025146000).

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Supporting Info.

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We have achieved the ring-opening and reconstruction reaction between N-heterocyclic carbene catalysts and 1,2-cyclobutenediones. By varying the type of N-heterocyclic carbene catalysts, we selectively obtained carbon-inserted 1,3-cyclopentanedione derivatives, as well as 1,2,3-cyclobutantrione derivatives featuring high oxidation states and high reactivity. Meanwhile, we isolated single-crystals of the key reaction intermediates for 1,2,3-cyclobutanetrione. This reaction afforded moderate to excellent yields (45%-98%). Combined with literature reports and single-crystal X-ray diffraction analysis, the two products were confirmed to proceed through completely distinct reaction pathways. Furthermore, this synthetic protocol features mild reaction conditions and simple operation, and the gram-scale scale-up experiment and derivatization transformations could also be smoothly implemented.

Key words: N-heterocyclic carbene, 1,2-cyclobutenedione, carbon-inserted, 1,3-cyclopentanedione, 1,2,3-cyclobutantrione