Citation: Ming Zhao,  Liqing Yang,  Yurong Xu. 氮杂环卡宾催化的亲核取代反应[J]. University Chemistry, ;2021, 36(4): 200404. doi: 10.3866/PKU.DXHX202004042 shu

氮杂环卡宾催化的亲核取代反应

  • Corresponding author: Ming Zhao, zhaomnwu@126.com
  • Received Date: 9 April 2020

  • 氮杂环卡宾作为有机催化剂催化的反应取得了巨大的研究进展;在反应中,氮杂环卡宾可以改变醛类化合物的反应极性,由亲电性转变为亲核性。本文主要对氮杂环卡宾催化的亲核取代反应进行了详细介绍,极性反转的醛可以通过SN1、SN2、SN2'、加成-消去、消去-加成过程和相应的底物发生反应。对于醛作为亲核试剂发生的取代反应,能够丰富和完善基础教学中醛酮反应知识点的内容,有利于学生了解学科的前沿发展,激发学生的探索和学习兴趣。
  • 加载中
    1. [1]

    2. [2]

      Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem. Rev. 2015, 115, 9307.

    3. [3]

    4. [4]

      Zhao, M.; Zhang, Y. T.; Chen, J.; Zhou, L. Asian J. Org. Chem. 2018, 7, 54.

    5. [5]

      Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296.

    6. [6]

      Yetra, S. R.; Patra, A.; Biju, A. T. Synthesis 2015, 47, 1357.

    7. [7]

      Langdon, S. M.; Wilde, M. M. D.; Thai, K.; Gravel, M. J. Am. Chem. Soc. 2014, 136, 7539.

    8. [8]

      Goodman, C. G.; Johnson, J. S. J. Am. Chem. Soc. 2014, 136, 14698.

    9. [9]

      Sun, L. H.; Liang, Z. Q.; Jia, W. Q.; Ye, S. Angew. Chem. Int. Ed. 2013, 52, 5803.

    10. [10]

      Zhang, J.; Xing, C.; Tiwari, B.; Chi, Y. R. J. Am. Chem. Soc. 2013, 135, 8113.

    11. [11]

      Lin, Q.; Li, Y.; Das, D. K.; Zhang, G.; Zhao, Z.; Yang, S.; Fang, X. Chem. Commun. 2016, 52, 6459.

    12. [12]

      Janssen-Müller, D.; Schedler, M.; Fleige, M.; Daniliuc, C. G.; Glorius, F. Angew. Chem. Int. Ed. 2015, 54, 12492.

    13. [13]

      He, J.; Zheng, J.; Liu, J.; She, X.; Pan, X. Org. Lett. 2006, 8, 4637.

    14. [14]

      Padmanaban, M.; Biju, A. T.; Glorius, F. Org. Lett. 2011, 13, 98.

    15. [15]

      Lin, L.; Li, Y.; Du, W.; Deng, W. P. Tetrahedron Lett. 2010, 51, 3571.

    16. [16]

      Singh, S.; Singh, P.; Rai, V. K.; Kapoor, R.; Yadav, L. D. S. Tetrahedron Lett. 2011, 52, 125.

    17. [17]

      Singh, P.; Singh, S.; Rai, V. K.; Yadav, L. D. S. Synlett 2010, 2649.

    18. [18]

      Zhao, M.; Yang, H.; Li, M. M.; Chen, J.; Zhou, L. Org. Lett. 2014, 16, 2904.

    19. [19]

      Zhao, M.; Chen, J.; Yang, H.; Zhou, L. Chem. Eur. J. 2017, 23, 2783.

    20. [20]

      Suzuki, Y.; Toyota, T.; Imada, F.; Sato, M.; Miyashita, A. Chem. Commun. 2003, 1314.

    21. [21]

      Li, Y.; Shi, F. Q.; He, Q. L.; You, S. L. Org. Lett. 2009, 11, 3182.

  • 加载中
    1. [1]

      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

    2. [2]

      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

    3. [3]

      Qiang ZhangYuanbiao HuangRong Cao . Imidazolium-Based Materials for CO2 Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040

    4. [4]

      Yongqing Kuang Jie Liu Jianjun Feng Wen Yang Shuanglian Cai Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

    5. [5]

      Yue Zhao Yanfei Li Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

    6. [6]

      Jiajie Li Xiaocong Ma Jufang Zheng Qiang Wan Xiaoshun Zhou Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117

    7. [7]

      Daojuan Cheng Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105

    8. [8]

      Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101

    9. [9]

      Yan KongWei WeiLekai XuChen 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

    10. [10]

      Jiaqi ANYunle LIUJianxuan SHANGYan GUOCe LIUFanlong ZENGAnyang LIWenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072

    11. [11]

      Feng Sha Xinyan Wu Ping Hu Wenqing Zhang Xiaoyang Luan Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082

    12. [12]

      Yan Qi Yueqin Yu Weisi Guo Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021

    13. [13]

      Aiyi Xin Jiawei Li Xinyang Ran Chuanjiang Fu Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031

    14. [14]

      Wentao Lin Wenfeng Wang Yaofeng Yuan Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095

    15. [15]

      Hui-Ying ChenHao-Lin ZhuPei-Qin LiaoXiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO2 Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046

    16. [16]

      Yi DINGPeiyu LIAOJianhua JIAMingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    17. [17]

      Ruonan LiShijie LiangYunhua XuCuifen ZhangZheng TangBaiqiao LiuWeiwei Li . Chlorine-Substituted Double-Cable Conjugated Polymers with Near-Infrared Absorption for Low Energy Loss Single-Component Organic Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(8): 2307037-0. doi: 10.3866/PKU.WHXB202307037

    18. [18]

      Haitao WangLianglang YuJizhou JiangArramelJing Zou . S-Doping of the N-Sites of g-C3N4 to Enhance Photocatalytic H2 Evolution Activity. Acta Physico-Chimica Sinica, 2024, 40(5): 2305047-0. doi: 10.3866/PKU.WHXB202305047

    19. [19]

      Fugui XIDu LIZhourui YANHui WANGJunyu XIANGZhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291

    20. [20]

      Weina Wang Lixia Feng Fengyi Liu Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022

Metrics
  • PDF Downloads(4)
  • Abstract views(330)
  • HTML views(15)

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