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

  • 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 RhII-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.
  • 加载中
    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. 

  • 加载中
    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 XiongN-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EZ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]

      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

    5. [5]

      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

    6. [6]

      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-. doi: 10.3866/PKU.WHXB202407005

    7. [7]

      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

    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]

      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

    10. [10]

      Jing WUPuzhen HUIHuilin ZHENGPingchuan YUANChunfei WANGHui WANGXiaoxia 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

    11. [11]

      Hong RAOYang HUYicong MAChunxin LÜWei ZHONGLihua 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

    12. [12]

      Hao Wu Zhen Liu Dachang Bai1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020

    13. [13]

      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

    14. [14]

      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

    15. [15]

      Ping ZHANGChenchen ZHAOXiaoyun CUIBing XIEYihan LIUHaiyu LINJiale ZHANGYu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014

    16. [16]

      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

    17. [17]

      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

    18. [18]

      Nan Xiao Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099

    19. [19]

      Xilin Zhao Xingyu Tu Zongxuan Li Rui Dong Bo Jiang Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106

    20. [20]

      Jinfeng Chu Lan Jin Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016

Metrics
  • PDF Downloads(0)
  • Abstract views(3261)
  • HTML views(1075)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return