Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 1978-1985.DOI: 10.6023/cjoc201404032 Previous Articles     Next Articles



蔡援a, 开铖a, 黄毅勇a, Verpoort Francisa,b,c   

  1. a. 武汉理工大学理学院化学系 武汉 430070;
    b. 武汉理工大学材料复合新技术国家重点实验室 武汉 430070;
    c. 比利时根特大学无机和物理化学系 比利时根特 9000
  • 收稿日期:2014-04-17 修回日期:2014-05-21 发布日期:2014-06-11
  • 通讯作者: 黄毅勇, Verpoort Francis;
  • 基金资助:

    国家自然科学基金(Nos. 21172027,21303128)资助项目.

Cyclic(alkyl)(amino)carbenes and the Research Prospect in Olefin Metathesis Reaction

Cai Yuana, Kai Chenga, Huang Yiyonga, Francis Verpoorta,b,c   

  1. a. Department of Chemistry, School of Science, Wuhan University of Technology, Wuhan 430070;
    b. State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070;
    c. Department of Inorganic and Physical Chemistry, Ghent University, Ghent 9000
  • Received:2014-04-17 Revised:2014-05-21 Published:2014-06-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21172027, 21303128).

Olefin metathesis has been one of the most important methods to construct carbon-carbon double bonds, which has been enabled by development of well-defined transition-metal catalysts (e.g. [L2X2Ru=CHR], L=PCy3). A significant gain to increase the catalyst stability and activity was achieved after replacing a single PCy3 ligand of L2X2Ru=CHR (L=PCy3) with cyclic biamino cabene, such as 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene (H2IMes). In 2005, Bertrand et al. discovered a novel ligand-yclic(alkyl)(amino)cabene (CAAC), which displayed more electron donating and more electrophilic in comparison with cyclic diamino cabene. It is logic that more electronegative amino group is replaced by alkyl group in CAAC. Furthermore, a quaternary carbon at the α position of carbene center of CAAC may make a big difference from cyclic diamino cabene, which can change the steric environment of CAAC easily and creat a chiral center next to the carbene. In this research prospect, synthesis, property and application of CAACs in olefin metathesis catalysis are introduced. Finally, the issues remained in this research area are summarized and an outlook for the development in the future is given.

Key words: olefin metathesis, catalyst, ruthenium, carbine