SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 6: 1713 - 1721

DOI: https://doi.org/10.6023/cjoc202111029

研究论文

咪唑离子官能化的HG-II型手性钌催化剂的制备及其催化的不对称烯烃复分解反应

  • 李涛 ,
  • 刘艺 ,
  • 白雪 ,
  • 周遵军 ,
  • 左鹏 ,
  • 麻妙锋 ,
  • 仲崇民 ,
  • 左亚杰
展开
  • a 西北农林科技大学化学与药学院 陕西杨凌 712100
    b 西北农林科技大学资源环境学院 陕西杨凌 712100

收稿日期: 2021-11-09

  修回日期: 2022-01-10

  网络出版日期: 2022-03-22

基金资助

国家自然科学基金(21673183)

收起

Preparation of Imidazolium Ion Functionalized HG-II Chiral Ruthenium Catalysts and Their Catalytic Performance in Asymmetric Olefin Metathesis

  • Tao Li ,
  • Yi Liu ,
  • Xue Bai ,
  • Zunjun Zhou ,
  • Peng Zuo ,
  • Miaofeng Ma ,
  • Chong-Min Zhong ,
  • Ya-Jie Zuo
Expand
  • a College of Chemistry and Pharmacy, Northwest Agriculture and Forestry University, Yangling, Shannxi 712100
    b College of Natural Resources and Environment, Northwest Agriculture and Forestry University, Yangling, Shannxi 712100
*E-mail: ;

Received date: 2021-11-09

  Revised date: 2022-01-10

  Online published: 2022-03-22

Supported by

National Natural Science Foundation of China(21673183)

Fold

摘要

钌催化的烯烃复分解反应的产率以及立体选择性主要决定于配体的性质. 在手性HG-II型催化剂的Hoveyda配体上修饰一个咪唑离子官能团, 并考察了所得催化剂在不对称关环复分解(ARCM)和不对称开环交叉烯烃复分解(AROCM)反应中的活性和立体选择性. 结果表明, 在ARCM反应中离子官能团的修饰与否对反应结果没有显著影响; 在AROCM反应中, 离子官能团的修饰对催化剂的活性没有影响, 但对某些产物的E/Z选择性和ee值有较明显的影响. 离子修饰使有些底物生成产物的E/Z值和ee值都有提高, 但对另一些底物则没有显著影响. 因此, 在AROCM反应中可以考虑用咪唑修饰的Hoveyda配体作为提高反应立体选择性的一个手段.

关键词： 咪唑离子; GH-II型钌催化剂; 手性钌催化剂; 不对称开环交叉烯烃复分解; Hoveyda配体

本文引用格式

李涛 , 刘艺 , 白雪 , 周遵军 , 左鹏 , 麻妙锋 , 仲崇民 , 左亚杰 . 咪唑离子官能化的HG-II型手性钌催化剂的制备及其催化的不对称烯烃复分解反应[J]. 有机化学, 2022 , 42(6) : 1713 -1721 . DOI: 10.6023/cjoc202111029

Abstract

The yield and stereoselectivity of the ruthenium-catalyzed olefin metathesis reaction are mainly determined by the nature of the ligands. In this study, two chiral HG-II ruthenium catalysts with imidazolium ion functionalized Hoveyda ligands were prepared, and their activity and stereoselectivity in the symmetric ring-closure metathesis (ARCM) and asymmetric ring-opening cross-olefin metathesis (AROCM) reactions were investigated. The results show that the modification of the Hoveyda ligands by ionic functional group produced no significant effect on ARCM reaction. For AROCM reaction, the ionic modification of the Hoveyda ligands shows an obvious improvment on both the E/Z selectivity and ee value for some products. Therefore, in the AROCM reaction, the Hoveyda ligands modified with imidazolium ion can be considered as a means to improve the stereoselectivity of the reaction.

Key words： imidazolium ion; GH-II ruthenium catalysts; chiral ruthenium catalysts; asymmetric ring opening cross metathesis; Hoveyda ligands

参考文献

[1]
Kress, S.; Blechert, S. Chem. Soc. Rev. 2012, 41, 4389.
[2]
Hoveyda, A. H.; Malcolmson, S. J.; Meek, S. J.; Zhugralin, A. R. Angew. Chem., Int. Ed. 2010, 49, 34.
[3]
Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225.
[4]
Funk, T. W.; Berlin, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 1840.
[5]
Berlin, J. M.; Goldberg, S. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 7591.
[6]
Hartung, J.; Dornan, P. K.; Grubbs, R. H. J. Am. Chem. Soc. 2014, 136, 13029.
[7]
Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954.
[8]
Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502.
[9]
Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 6877.
[10]
Cortez, G. A.; Baxter, C. A.; Schrock, R. R.; Hoveyda, A. H. Org. Lett. 2007, 9, 2871.
[11]
Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2007, 129, 3824.
[12]
Fournier, P.-A.; Collins, S. K. Organometallics 2007, 26, 2945.
[13]
Fournier, P.-A.; Savoie, J.; Stenne, B.; Bédard, M.; Grandbois, A.; Collins, S. K. Chem. Eur. J. 2008, 14, 8690.
[14]
Grandbois, A.; Collins, S. K. Chem. Eur. J. 2008, 14, 9323.
[15]
Savoie, J.; Stenne, B.; Collins, S. K. Adv. Synth. Catal. 2009, 351, 1826.
[16]
Stenne, B.; Timperio, J.; Savoie, J.; Dudding, T.; Collins, S. K. Org. Lett. 2010, 12, 2032.
[17]
Paradiso, V.; Bertolasi, V.; Costabile, C.; Grisi, F. Dalton Trans. 2016, 45, 561.
[18]
Paradiso, V.; Bertolasi, V.; Costabile, C.; Caruso, T.; Dąbrowski, M.; Grela, K.; Grisi, F. Organometallics 2017, 36, 3692.
[19]
Ambrosio, C.; Paradiso, V.; Costabile, C.; Bertolasi, V.; Caruso, T.; Grisi, F. Dalton Trans. 2018, 47, 6615.
[20]
Grisi, F.; Costabile, C.; Gallo, E.; Mariconda, A.; Tedesco, C.; Longo, P. Organometallics 2008, 27, 4649.
[21]
Tiede, S.; Berger, A.; Schlesiger, D.; Rost, D.; Lühl, A.; Blechert, S. Angew. Chem., Int. Ed. 2010, 49, 3972.
[22]
Kannenberg, A.; Rost, D.; Eibauer, S.; Tiede, S.; Blechert, S. Angew. Chem., Int. Ed. 2011, 50, 3299.
[23]
Ivry, E.; Ben-Asuly, A.; Goldberg, I.; Lemcoff, N. G. Chem. Commun. 2015, 51, 3870.
[24]
Chen, S.-W.; Zhang, Z.-C.; Ma, M.; Zhong, C.-M.; Lee, S.-G. Org. Lett. 2014, 16, 4969.
[25]
Chen, S.-W.; Zhang, Z.-C.; Zhai, N.-N.; Zhong, C.-M.; Lee, S.-G. Tetrahedron 2015, 71, 648.
[26]
Chen, X.-L.; Li, X.-Y.; Li, S.-S.; Bai, X.; Li, T.; Goud, E. Y.; Zhong, C.-M.; Zuo, Y.-J. Russ. J. Gen. Chem. 2020, 90, 2163.
[27]
For the synthesis of the triflate analog of chiral imidazolinium salt 13, see: Zhang, J.; Su, X.; Fu, J.; Shi, M. Chem. Commun. 2011, 47, 12541.
[28]
Costabile, C.; Cavallo, L. J. Am. Chem. Soc. 2004, 126, 9592.
[29]
June, S. L.; Laleh, T.; James, A. G.; Curtis, M.; Arnold, L. R.; Linda, H. D. Chem. Eur. J. 2013, 19, 6374.
Options
文章导航

/

〈 〉