有机化学 ›› 2019, Vol. 39 ›› Issue (5): 1404-1410.DOI: 10.6023/cjoc201812035 上一篇    下一篇

研究论文

氮杂环卡宾(NHC)催化下多取代环戊烯的串联合成

李莎, 杨雯涵, 罗鲜, 姚昌盛   

  1. 江苏省功能材料绿色合成重点实验室 江苏师范大学化学与材料科学学院 徐州 221116
  • 收稿日期:2018-12-19 修回日期:2019-01-09 出版日期:2019-05-25 发布日期:2019-01-18
  • 通讯作者: 姚昌盛 E-mail:csyao@jsnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21871113,21372101)资助项目.

An Efficient N-Heterocyclic Carbene (NHC)-Catalyzed Synthesis of Polysubstituted Cyclopentene

Li Sha, Yang Wenhan, Luo Xian, Yao Changsheng   

  1. Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116
  • Received:2018-12-19 Revised:2019-01-09 Online:2019-05-25 Published:2019-01-18
  • Contact: 10.6023/cjoc201812035 E-mail:csyao@jsnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21871113, 21372101).

在氮杂环卡宾(N-heterocyclic carbene,NHC)催化下,αβ-不饱和羧酸经过原位活化后与2-(2-氧代-2-芳乙基)丙二腈发生Michael加成、羟醛缩合、脱羧等反应,一锅法合成了多取代环戊烯类化合物.该方法具有底物范围广、原料易得、反应条件温和、产率高、操作简便等优点,为多官能化环戊烯类化合物的高效合成提供了新思路.

关键词: 氮杂环卡宾(NHC), α,β-不饱和羧酸, 2-(2-氧代芳乙基)丙二腈, 多取代环戊烯, 串联反应

An one-pot, cascade assembly of polysubstituted cyclopentene was realized via the N-heterocyclic carbene (NHC)-catalyzed annulation of the in situ activated α,β-unsaturated carboxylic acid with 2-(2-oxo-2-arylethyl)malononitrile through the sequence of Michael addition, aldol condesation and decarboxylation. This method could serve as a new attractive strategy for the practical syntheses of multi-functionalized cyclopentene derivatives with broad substrate scope, readily availability of starting materials, mild reaction conditions, excellent yields and operational simplicity.

Key words: N-heterocyclic carbene (NHC), α,β-unsaturated carboxylic acid, 2-(2-oxo-2-arylethyl)malononitrile, poly-substituted cyclopentene, cascade reaction