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2023 , Vol. 43 >Issue 3: 1084 - 1090

DOI: https://doi.org/10.6023/cjoc202301011

研究论文

氮杂环卡宾(NHC)催化[4+3]环加成反应构建4-氨基苯并环庚烯内酯

  • 戴春波 ,
  • 夏思奇 ,
  • 陈晓玉 ,
  • 杨丽敏
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  • 杭州师范大学材料与化学化工学院 有机硅化学及材料技术教育部重点实验室 杭州 311121
† 共同第一作者.

收稿日期: 2023-01-10

  修回日期: 2023-02-20

  网络出版日期: 2023-03-01

基金资助

国家自然科学基金(22271071); 浙江省自然科学基金(LY20B020010)

收起

N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons

  • Chunbo Dai ,
  • Siqi Xia ,
  • Xiaoyu Chen ,
  • Limin Yang
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  • Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121
† These authors contributed equally to this work.
* Corresponding author. E-mail:

Received date: 2023-01-10

  Revised date: 2023-02-20

  Online published: 2023-03-01

Supported by

National Natural Science Foundation of China(22271071); Natural Science Foundation of Zhejiang Province(LY20B020010)

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摘要

报道了4-氨基苯并环庚烯内酯的合成方法, 在氮杂环卡宾的催化作用下, γ-氯醛与亚胺醌化合物经过[4+3]环加成反应生成4-氨基苯并环庚烯内酯, 产率良好, 且反应产物单一, 反应条件温和, 操作简便, 符合绿色化学原则. 为了探究氮杂环卡宾在该反应的位点选择性所起的作用, 利用密度泛函理论进行了理论研究, 研究表明形变力是导致位点选择差异性的主要原因.

关键词： 氮杂环卡宾; 有机催化; [4+3]环加成反应; 位点选择性; 4-氨基苯并环庚烯内酯

本文引用格式

戴春波 , 夏思奇 , 陈晓玉 , 杨丽敏 . 氮杂环卡宾(NHC)催化[4+3]环加成反应构建4-氨基苯并环庚烯内酯[J]. 有机化学, 2023 , 43(3) : 1084 -1090 . DOI: 10.6023/cjoc202301011

Abstract

A highly efficient N-heterocyclic carbene (NHC) catalyzed formal [3+4] cycloaddition reaction of γ-chloroenal with iminoquinones has been developed, producing 4-aminobenzoheptenolactone derivatives in good yields. In order to explore the role of nitroheterocyclic carbene in the site selectivity of the reaction, a theoretical study was carried out using density functional theory. The study showed that the deformation force was the main reason for the difference in site selection.

Key words： N-heterocyclic carbene (NHC); organocatalysis; [4+3] cycloaddition; site selectivity; 4-aminobenzoheptenolactone

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