Citation: Zhou Peng, Qiu Huihua, Shi Jicheng. Palladium Catalyzed Cascade Cyclization of ortho-Alkenyl Bromobenzenes and Internal Alkynes for Multisubstituted Indenes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 425-431. doi: 10.6023/cjoc201508025 shu

Palladium Catalyzed Cascade Cyclization of ortho-Alkenyl Bromobenzenes and Internal Alkynes for Multisubstituted Indenes

  • Corresponding author: Zhou Peng, zzd83@aliyun.com
  • Received Date: 25 August 2015
    Revised Date: 12 October 2015

    Fund Project: the Natural Science Foundation of Guangdong Province S2013040014944the National Natural Science Foundation of China 21272037

Figures(2)

  • This paper developed a new method for the construction of polysubstituted indenes. And a number of multisubstituted indenes have been synthesized from functional o-alkenyl bromobenzenes and alkynes in good yields through palladium-catalyzed annulations in N, N-dimethylformamide (DMF) taking Na2CO3 as base. The methodology tolerates a variety of functional groups with simple reaction conditions and the catalyst can be reused.
  • 加载中
    1. [1]

      Some selected examples, please see: (a) Alcalde, E.; Mesquida, N.; López-Pérez, S.; Frigola, J.; Mercè R. J. Med. Chem. 2009, 52, 675.
      (b) Citta, A.; Folda, A.; Bindoli, A.; Pigeon, P.; Top, S.; Vessières, A.; Salmain, M.; Jaouen, G.; Rigobello, M. P. J. Med. Chem. 2014, 57, 8849.
      (c) Xie, J.; Zhou, Q. Acta Chim. Sinica 2014, 72, 778 (in Chinese).
      (谢建华, 周其林, 化学学报, 2014, 72, 778.)

    2. [2]

      Some selected examples, please see: (a) Liu, L.; Fan, Y.; He, Q.; Zhang, Y.; Zhang-Negrerie, D.; Huang, J.; Du, Y.; Zhao, K. J. Org. Chem. 2012, 77, 3997.
      (b) Mróz, W.; Villafiorita-Monteleone, F.; Pasini, M.; Grisci, G.; Paolino, M.; Razzano, V.; Cappelli, A.; Botta, C. Mater. Lett. 2015, 142, 197.
      (c) Tehfe, M.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.; Lalevée, J. Macromolecules 2013, 46, 3332.

    3. [3]

      Some selected examples, please see: (a) Rao, Y.; Liu, M.; Yin, G. Chin. J. Org. Chem. 2015, 35, 719 (in Chinese).
      (饶寅, 刘美林, 殷国栋, 有机化学, 2015, 35, 719.)
      (b) Zhou, F.; Yang, M.; Lu, X. Org. Lett. 2009, 11, 1405.
      (c) Bu, X.; Hong, J.; Zhou, X. Adv. Synth. Catal. 2011, 353, 2111.
      (d) Huang, X.; Yang, X.; Song, R.; Li, J. J. Org. Chem. 2014, 79, 1025.
      (e) Li, G.; Hu, H.; Kan, Y.; Ma, K. Chin. J. Org. Chem. 2014, 34, 903 (in Chinese).
      (李国栋, 胡华友, 阚玉和, 马奎蓉, 有机化学, 2015, 34, 903.)
      (f) Tan, F.; Chen, J.; Wang, P.; Xiao, W. Acta Chim. Sinica 2014, 72, 836 (in Chinese).
      (谭芬, 陈加荣, 王萍, 肖文精, 化学学报, 2014, 72, 836.)

    4. [4]

      Some selected examples, please see: (a) Zhu, L.; Du, G.; Yang, W.; Min, L.; Liu, X.; Huang, S.; Han, Y.; Lee, C.-S. Chin. J. Org. Chem. 2013, 33, 2031 (in Chinese).
      (朱礼志, 杜广延, 杨炜, 闵龙, 刘小卒, 黄双平, 韩叶俭, 李志成, 有机化学, 2013, 33, 2031.)
      (b) Hu, L.; Gao, L.; Wan, C.; Wang, Z. Acta Chim. Sinica 2013, 71, 1603 (in Chinese).
      (胡露丹, 高令峰, 万常峰, 汪志勇, 化学学报, 2013, 71, 1603.)
      (c) Li, Y.; Wang, J.; Wei, X.; Yang, S. Chin. J. Org. Chem. 2015, 35, 638 (in Chinese).
      (李永红, 王君姣, 魏小红, 杨尚东, 有机化学, 2015, 35, 638.)
      (d) Li, J.; Li, C.; Yang, S.; Luo, W. Chin. J. Org. Chem. 2015, 35, 898 (in Chinese).
      (李建晓, 李春生, 杨少容, 罗维, 有机化学, 2015, 35, 898.)

    5. [5]

      Selected reviews on Pd-catalyzed annulation of functional aryl halides: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
      (b) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.

    6. [6]

      Shibata, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 1781.  doi: 10.1021/ol0503743

    7. [7]

      Shibata, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2007, 349, 2317.  doi: 10.1002/(ISSN)1615-4169

    8. [8]

      Liao, T.-G.; Wang, Q.-A.; Fang, W.-Q.; Zhu, H.-J. Chin. J. Org. Chem. 2006, 26, 685 (in Chinese).
       

    9. [9]

      Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 45, 5406.
       

  • 加载中
    1. [1]

      Renxiao Liang Zhe Zhong Zhangling Jin Lijuan Shi Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024

    2. [2]

      Zhengyu Zhou Huiqin Yao Youlin Wu Teng Li Noritatsu Tsubaki Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010

    3. [3]

      Jinyao Du Xingchao Zang Ningning Xu Yongjun Liu Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

    4. [4]

      Tongyan Yu Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070

    5. [5]

      Jie ZHAOSen LIUQikang YINXiaoqing LUZhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385

    6. [6]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    7. [7]

      Dongheng WANGSi LIShuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

    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]

      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

    10. [10]

      Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047

    11. [11]

      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

    12. [12]

      Hong Lu Yidie Zhai Xingxing Cheng Yujia Gao Qing Wei Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074

    13. [13]

      Guojie Xu Fang Yu Yunxia Wang Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060

    14. [14]

      Yuanyi Lu Jun Zhao Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088

    15. [15]

      Zhuoyan Lv Yangming Ding Leilei Kang Lin Li Xiao Yan Liu Aiqin Wang Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015

    16. [16]

      Hongting Yan Aili Feng Rongxiu Zhu Lei Liu Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010

    17. [17]

      Aili Feng Xin Lu Peng Liu Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072

    18. [18]

      Xueting Cao Shuangshuang Cha Ming Gong . 电催化反应中的界面双电层:理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041

    19. [19]

      Pengzi Wang Wenjing Xiao Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090

    20. [20]

      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

Metrics
  • PDF Downloads(0)
  • Abstract views(951)
  • HTML views(156)

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