Hydrogen-Bonding Effects in Ruthenium-Catalyzed Olefin Metathesis

doi:10.6023/cjoc201805001

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2491-2500.DOI: 10.6023/cjoc201805001 Previous Articles Next Articles

Reviews

钌催化烯烃复分解反应中的氢键效应

颜廷斌, 刘跃辉, 沈悦海

昆明理工大学生命科学与技术学院昆明 650500

收稿日期:2018-05-02 修回日期:2018-06-12 发布日期:2018-06-29
通讯作者: 沈悦海,E-mail:yuehaishen@kmust.edu.cn E-mail:yuehaishen@kmust.edu.cn
基金资助:
国家自然科学基金（No.21662022）资助项目.

Hydrogen-Bonding Effects in Ruthenium-Catalyzed Olefin Metathesis

Yan Tingbin, Liu Yuehui, Shen Yuehai

Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500

Received:2018-05-02 Revised:2018-06-12 Published:2018-06-29
Contact: 10.6023/cjoc201805001 E-mail:yuehaishen@kmust.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21662022).

Olefin metathesis is among the most popular synthetic methods over the past two decades. Owing to the good functional group tolerance of ruthenium catalysts, hydrogen bonding has emerged as a powerful controlling element for olefin metathesis recently. Recent studies demonstrated that the hydrogen bonding between ruthenium catalyst and certain types of substrates or additives could significantly improve the rate, chemoselectivity and stereoselectivity of olefin metathesis, while the self-assembly of substrates could be driven by intramolecular or intermolecular hydrogen bonding and result in highly selective reactions. In this review, the development and application of hydrogen bonding-promoted ruthenium-catalyzed olefin metathesis reactions are summarized, and the mechanism insights into these systems are highlighted.

Key words: olefin metathesis, ruthenium-carbene complex, catalysis, hydrogen bonding

Cite this article

Yan Tingbin, Liu Yuehui, Shen Yuehai. Hydrogen-Bonding Effects in Ruthenium-Catalyzed Olefin Metathesis[J]. Chin. J. Org. Chem., 2018, 38(10): 2491-2500.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Hoveyda, A. H.; Zhugralin, A. R. Nature 2007, 450, 243.
[2] Zielinski, G. K.; Grela, K. Chem.-Eur. J. 2016, 22, 9440.
[3] Kotha, S.; Dipak, M. K. Tetrahedron 2012, 68, 397.
[4] Fürstner, A. Chem. Commun. 2011, 47, 6505.
[5] Han, J. C.; Li, C. C. Synlett 2015, 26, 1289.
[6] Tomasek, J.; Schatz, J. Green Chem. 2013, 15, 2317.
[7] Levin, E.; Ivry, E.; Diesendruck, C. E.; Lemcoff, N. G. Chem. Rev. 2015, 115, 4607.
[8] Lin, Y. A.; Davis, B. G. Beilstein J. Org. Chem. 2010, 6, 1219.
[9] Aullon, G.; Bellamy, D.; Brammer, L.; Bruton, E. A.; Orpen, A. G. Chem. Commun. 1998, 653.
[10] Forman, G. S.; McConnell, A. E.; Tooze, R. P.; van Rensburg, W. J.; Meyer, W. H.; Kirk, M. M.; Dwyer, C. L.; Serfontein, D. W. Organometallics 2005, 24, 4528.
[11] Imahori, T.; Ojima, H.; Yoshimura, Y.; Takahata, H. Chem.-Eur. J. 2008, 14, 10762.
[12] Hoveyda, A. H.; Lombardi, P. J.; O'Brien, R. V.; Zhugralin, A. R. J. Am. Chem. Soc. 2009, 131, 8378.
[13] Feng, L.; Liu, Y. H.; Hou, B.; Yuan, Z. F.; Yu, F. C.; Yan, T. B.; Qin, Q.; Ji, R. G.; Li, Y. M.; Shen, Y. H.; Zuo, Z. L. Org. Biomol. Chem. 2016, 14, 10705.
[14] Hoye, T. R.; Zhao, H. Y. Org. Lett. 1999, 1, 1123.
[15] Schmidt, B.; Nave, S. Adv. Synth. Catal. 2007, 349, 215.
[16] Nicolaou, K. C.; Leung, G. Y. C.; Dethe, D. H.; Guduru, R.; Sun, Y. P.; Lim, C. S.; Chen, D. Y. K. J. Am. Chem. Soc. 2008, 130, 10019.
[17] Matsuya, Y.; Yamakawa, Y.; Tohda, C.; Teshigawara, K.; Yamada, M.; Nemoto, H. Org. Lett. 2009, 11, 3970.
[18] Sugimoto, K.; Yajima, H.; Hayashi, Y.; Minato, D.; Terasaki, S.; Tohda, C.; Matsuya, Y. Org. Lett. 2015, 17, 5910.
[19] Chowdhury, P. S.; Gupta, P.; Kumar, P. Tetrahedron Lett. 2009, 50, 7188.
[20] Trost, B. M.; Dong, G. B.; Vance, J. A. Chem.-Eur. J. 2010, 16, 6265.
[21] Srihari, P.; Kumaraswamy, B.; Shankar, P.; Ravishashidhar, V.; Yadav, J. S. Tetrahedron Lett. 2010, 51, 6174.
[22] Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 209.
[23] Lautens, M.; Maddess, M. L. Org. Lett. 2004, 6, 1883.
[24] Fuwa, H.; Yamaguchi, H.; Sasaki, M. Org. Lett. 2010, 12, 1848.
[25] Fuwa, H.; Saito, A.; Sasaki, M. Angew. Chem., Int. Ed. 2010, 49, 3041.
[26] Huang, Q. Y.; Herdewijn, P. J. Org. Chem. 2011, 76, 3742.
[27] Khan, R. K. M.; Torker, S.; Hoveyda, A. H. J. Am. Chem. Soc. 2013, 135, 10258.
[28] Koh, M. J.; Khan, R. K. M.; Torker, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2014, 53, 1968.
[29] Lee, K. S.; Choi, T. L. Org. Lett. 2011, 13, 3908.
[30] Forman, G. S.; Tooze, R. P. J. Organomet. Chem. 2005, 690, 5863.
[31] Schmidt, B.; Staude, L. J. Org. Chem. 2009, 74, 9237.
[32] Schmidt, B.; Kunz, O.; Biernat, A. J. Org. Chem. 2010, 75, 2389.
[33] Schmidt, B.; Hauke, S. Org. Biomol. Chem. 2013, 11, 4194.
[34] Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855.
[35] Saha, B.; Das, D.; Banerji, B.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6467.
[36] Cromm, P. M.; Spiegel, J.; Grossmann, T. N. ACS Chem. Biol. 2015, 10, 1362.
[37] Cromm, P. M.; Schaubach, S.; Spiegel, J.; Fürstner, A.; Grossmann, T. N.; Waldmann, H. Nat. Commun. 2016, 7, 11300.
[38] Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364.
[39] Yang, X. W.; Gong, B. Angew. Chem., Int. Ed. 2005, 44, 1352.
[40] Zeng, J. S.; Wang, W.; Deng, P. C.; Feng, W.; Zhou, J. J.; Yang, Y. Y.; Yuan, L. H.; Yamamoto, K.; Gong, B. Org. Lett. 2011, 13, 3798.
[41] Kidd, T. J.; Leigh, D. A.; Wilson, A. J. J. Am. Chem. Soc. 1999, 121, 1599.
[42] Hannam, J. S.; Kidd, T. J.; Leigh, D. A.; Wilson, A. J. Org. Lett. 2003, 5, 1907.
[43] Wisner, J. A.; Beer, P. D.; Drew, M. G. B.; Sambrook, M. R. J. Am. Chem. Soc. 2002, 124, 12469.
[44] Kilbinger, A. F. M.; Cantrill, S. J.; Waltman, A. W.; Day, M. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 3281.
[45] Scherman, O. A.; Ligthart, G. B. W. L.; Ohkawa, H.; Sijbesma, R. P.; Meijer, E. W. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 11850.
[46] Liu, X. G.; Xu, J. F.; Wang, Z. Q.; Zhang, X. Polym. Chem. 2016, 7, 2333.
[47] Neal, J. A.; Mozhdehi, D.; Guan, Z. J. Am. Chem. Soc. 2015, 137, 4846.
[48] Trita, A. S.; Roisnel, T.; Mongin, F.; Chevallier, F. Org. Lett. 2013, 15, 3798.

钌催化烯烃复分解反应中的氢键效应

Hydrogen-Bonding Effects in Ruthenium-Catalyzed Olefin Metathesis

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[3]	Shuang Yang, Xinqiang Fang. Kinetic Resolutions Enabled by N-Heterocyclic Carbene Catalysis: An Update [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 448-480.
[4]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[5]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[6]	Jing Huang, Yihua Yang, Zhanhui Zhang, Shouxin Liu. Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 409-420.
[7]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[8]	Yang Li, Yanan Dong, Yuehui Li. Efficient Synthesis of Nitrile Compounds through Amide Conversion via N-Boroamide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 638-643.
[9]	Sida Li, Xin Cui, Xing-Zhong Shu, Lipeng Wu. Titanium-Catalyzed Synthesis of 1,1-Diborylalkanes from Aryl Alkenes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 631-637.
[10]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[11]	Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu. Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 195-203.
[12]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[13]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[14]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[15]	Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.