Citation: Huang Jiapian, Zhou Hao, Chen Zhiyuan. Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1555-1563. doi: 10.6023/cjoc201601042 shu

Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives

1.
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Chen Zhiyuan, zchen@jxnu.edu.cn
Received Date: 29 January 2016
Revised Date: 28 February 2016

Fund Project: the National Natural Science Foundation of China No. 21462022

Figures(15)

Carbenes are very useful key intermediates in organic synthesis, which generally display high reactivity in chemical transformations. Metallocarbenes can be regarded as metal stabilized organic carbenes. The research progress of the metallocarbene formation and the related reactions based on triazole compounds are reviewed in this work. The Rh^II-catalyzed metallocarbenes derived from N-sulfonyl-1,2,3-triazoles, as well as the subsequent insertion reactions into other reaction systems to generate new C-C or C-hetero bonds, are specially focused.
- transition-metal-catalysis,
- metallocarbenes,
- triazole compounds,
- carbo and heterocyclic compounds
1. [1]
  Fischer, E. O. Angew. Chem., Int. Ed. 1974, 86, 651. (b) Schrock, R. R. Acc. Chem. Soc. 1979, 12, 98.
2. [2]
3. [3]
  Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861. (b) Davies, H. M. L.; Alford, J. Chem. Soc. Rev. 2014, 43, 5151.
4. [4]
  Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.
5. [5]
  Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
6. [6]
  For a review, see: Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862.
7. [7]
  Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
8. [8]
  Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972. (b) Chuprakov, S.; Kwok, S. W.; Zhang, L.; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034.
9. [9]
  Grimster, N.; Zhang, L.; Fokin, V. V. J. Am. Chem. Soc. 2010, 132, 2510.
10. [10]
  Chuprakov, S.; Kwok, S. W.; Zhang, L; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034.
11. [11]
  For recent application examples, see: (a) Davies, H. M. L.; Nagashima, T.; Klino, J. L. Org. Lett. 2000, 2, 823. (b) Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233. (c) Davies, H. M. L.; Coleman, M. G.; Ventura, D. L. Org. Lett. 2007, 9, 4971.
12. [12]
  Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett. 2006, 8, 3437. (b) Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625. (c) Denton, J. R.; Davies, H. M. L. Org. Lett. 2009, 11, 787.
13. [13]
14. [14]
  Horneff, T.; Chuprakov, S.; Chernyak, V.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
15. [15]
  Connell, R.; Scavo, F.; Helquist, P.; Akermark, B. Tetrahedron Lett. 1986, 27, 5559.
16. [16]
  Selander, N.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 2477.
17. [17]
  Chuprakov, S.; Malik, J. A.; Zibinsky, M.; Fokin, V. V. J. Am. Chem. Soc. 2011, 133, 10352.
18. [18]
  Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670.
19. [19]
  Chuprakov, S.; Kwok, S. W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652.
20. [20]
  Chuprakov, S.; Worrell, B. T.; Selander, N.; Rakesh, K. S.; Fokin, V. V. J. Am. Chem. Soc. 2014, 136, 195.
21. [21]
  For recent development of triazoles see: (a) Jillian, E. S.; Huw, M. L.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802. (b) Jung, D. J.; Jeon, H. J.; Kim, J. H.; Kim, Y.; Lee, S. G.. Org. Lett. 2014, 16, 2208. (c) Yadagiri, D.; Anbarasan, P. Org. Lett. 2014, 16, 2510. (d) Shen, H.-J.; Fu, J.-K.; Gong, J.-X.; Yang, Z. Org. Lett. 2014, 16, 5588. (e) Xing, Y.-P.; Sheng, G.-R.; Wang, J.; Lu, P.; Wang, Y.-G. Org. Lett. 2014, 16, 1244. (f) Chattopadhyay, B.; Gevorgyan, V. Org. Lett. 2011, 13, 3746.
22. [22]
  Shi, Y.; Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2014, 53, 14191.
23. [23]
  Brendan, T. P.; Samantha, A. G.; Huw, M. L.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716.
24. [24]
  Lindsay, V. N. G.; Viart, H. M. F.; Sarpong, R. J. Am. Chem. Soc., 2015, 137, 8368.
25. [25]
  Yadagiri, D.; Anbarasan, P. Chem. Sci. 2015, 6, 5847.
26. [26]
  Zhang, Y.-S.; Tang, X.-Y.; Shi, M. Chem. Commun. 2014, 50, 15971.
27. [27]
  Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802.
28. [28]
  Huang, J.-P.; Yang, Y.; Chen, Z.-Y. Adv. Synth. Catal. 2016, 358, 201.
29. [29]
  Yang, Y.; Zhou, M.-B.; Ouyang, X.-H.; Pi, R.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 6595.
30. [30]
  Tetsuji, K.; Keiichiro, F. Heterocycles 1975, 3, 931. (b) Renfroe, B.; Harrington, C.; Proctor, P. T. Heterocyclic Compounds: Azepines, Wiley Interscience, New York, 1984. (c) Ganellin, C. R.; Triggle, D. J. Dictionary of Pharmacological Agents, Chapman & Hall/CRC, London, 1996.
31. [31]
  Miura, T.; Yamauchi, M.; Murakami, M. Chem. Commun. 2009, 1470.
32. [32]
  Miura, T.; Hiraga, K.; Biyajima, T.; Nakamuro, T.; Murakami, M. Org. Lett. 2013, 15, 3298.
33. [33]
  Helan, V.; Gulevich, A. V.; Gevorgyan, V. Chem. Sci. 2015, 6, 1928.
34. [34]
  Chuprakov, S.; Hwang, H. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.
1. [1]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
2. [2]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
3. [3]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
4. [4]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
5. [5]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
6. [6]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
7. [7]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-0. doi: 10.3866/PKU.WHXB202407005
8. [8]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
9. [9]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
10. [10]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
11. [11]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
12. [12]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
13. [13]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
14. [14]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
15. [15]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
16. [16]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
17. [17]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
18. [18]
  Lu Zhuoran , Li Shengkai , Lu Yuxuan , Wang Shuangyin , Zou Yuqin . Cleavage of C―C Bonds for Biomass Upgrading on Transition Metal Electrocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2306003-0. doi: 10.3866/PKU.WHXB202306003
19. [19]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
20. [20]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(3357)
HTML views(1086)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142