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

doi:10.6023/cjoc201404032

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

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环(烷基)(氨基)卡宾及其在烯烃复分解反应中的研究展望

蔡援^a, 开铖^a, 黄毅勇^a, Verpoort Francis^a,b,c

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 E-mail:huangyy@whut.edu.cn;francis@whut.edu.cn
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 Yuan^a, Kai Cheng^a, Huang Yiyong^a, Francis Verpoort^a,b,c

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

Cite this article

Cai Yuan, Kai Cheng, Huang Yiyong, Francis Verpoort. Cyclic(alkyl)(amino)carbenes and the Research Prospect in Olefin Metathesis Reaction[J]. Chin. J. Org. Chem., 2014, 34(10): 1978-1985.

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环(烷基)(氨基)卡宾及其在烯烃复分解反应中的研究展望

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

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