Citation: Zhao Zhuanxia, Wang Junjiao, Huang Danfeng, Yang Zheng, Zhao Fangxia, Hu Yongqin, Xu Weigang, Hu Yulai. Study on Tin Powder-Promoted Allylation of 3-Aryl-3-hydroxy-2-oxindoles[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 2026-2034. doi: 10.6023/cjoc202003002 shu

Study on Tin Powder-Promoted Allylation of 3-Aryl-3-hydroxy-2-oxindoles

  • Corresponding author: Huang Danfeng, huangdf@nwnu.edu.cn
  • Received Date: 1 March 2020
    Revised Date: 9 April 2020
    Available Online: 23 April 2020

    Fund Project: the National Natural Science Foundation of China 21861033the National Natural Science Foundation of China 21462037the Natural Science Foundation of Gansu Province 18JR3RA091Project supported by the National Natural Science Foundation of China (Nos. 21861033, 21462037), and the Natural Science Foundation of Gansu Province (No. 18JR3RA091)

Figures(4)

  • An efficient tin-powder-promoted C-C coupling reaction of 3-aryl-3-hydroxy-2-oxindoles with allyl bromide was disclosed, which makes tin-powder-promoted reactions beyond 1, 2-addition to C=O or C=N double bounds, and provides a convenient and facile protocol for the synthesis of potentially bioactive 3, 3'-disubstituted-2-oxindoles in good to excellent yields. The method is highly efficient and environmentally benign with low cost and concise manipulation.
  • 加载中
    1. [1]

      (a) Roy, U. K.; Roy, S. Chem. Rev. 2010, 110, 2472.
      (b) Zha, Z.; Hui, A.; Zhou, Y.; Miao, Q.; Wang, Z.; Zhang, H. Org. Lett. 2005, 7, 1903.
      (c) Crich, D.; Grant, D.; Krishnamurthy, V.; Patel, M. Acc. Chem. Res. 2007, 40, 453.
      (d) Davies, A. G.; Gielen, M.; Pannell, K. H.; Tiekink, E. R. T. Tin chemistry: Fundamentals, Frontiers, and Applications; John Wiley & Sons, Chichester, U.K., 2008.

    2. [2]

      (a) Hoch, M. Appl. Geochem. 2001, 16, 719.
      (b) Amouroux, D.; Tessier, E.; Donard, O. F. X. Environ. Sci. Technol. 2000, 34, 988.
      (c) Lukevics, E.; Pudova, O. Biological Activity of Organotin and Organolead Compounds. In the Chemistry of Organic Germanium, Tin and Lead Compounds, Vol. 2, Ed.: Rappoport, Z., John Wiley and Sons, Chichester, 2002, p. 1685.
      (d) Barnes, J. M.; Stoner, H. B. Pharmacol. Rev. 1959, 11, 211.

    3. [3]

      (a) Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026.
      (b) Teo, Y.-C.; Goh, J.-D.; Loh, T.-P. Org. Lett. 2005, 7, 2743.
      (c) Suzuki, T.; Atsumi, J.-I.; Sengoku, T.; Takahashi, M.; Yoda, H. J. Organomet. Chem. 2010, 695, 128.
      (d) Deng, D.; Liu, P.; Ji, B.; Wang, L.; Fu, W. Tetrahedron Lett. 2010, 51, 5567.
      (e) Cormier, M.; Ahmad, M.; Maddaluno, J.; Paolis, M. D. Organometallics 2017, 36, 4920.
      (f) Mahajani, N. S.; Chisholm, J. D. Org. Biomol. Chem. 2018, 16, 4008.

    4. [4]

      Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 10, 1527.  doi: 10.1246/cl.1981.1527

    5. [5]

      (a) Elaas, N. A.; Elaas, W. A.; Huang, D.; Hu, Y.; Wang, K.-H. Curr. Org. Synth. 2017, 14, 1156.
      (b) Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958.
      (c) Alcaide, B.; Almendros, P.; Rodríguez-Acebes, R. J. Org. Chem. 2005, 70, 2713.
      (d) Appelt, H. R.; Limberger, J. B.; Weber, M.; Rodrigues, O. E. D.; Oliveira, J. S.; Lüdtke, D. S.; Braga, A. L. Tetrahedron Lett. 2008, 49, 4956.
      (e) Thorat, P. B.; Goswami, S. V.; Bhusare, S. R. Tetrahedron: Asymmetry 2013, 24, 1324.
      (f) Wang, Z.; Zha, Z.; Zhou, C. Org. Lett. 2002, 4, 1683.
      (g) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2001, 66, 5208.
      (h) Estevam, I. H. S.; Bieber, L. W. Tetrahedron Lett. 2003, 44, 667

    6. [6]

      (a) Lin, M.-H.; Lin, L.-Z.; Chuang, T.-H.; Liu, H.-J. Tetrahedron 2012, 68, 2630.
      (b) Lin, M.-H.; Hung, S.-F.; Lin, L.-Z.; Tsai, W.-S.; Chuang, T.-H. Org. Lett. 2011, 13, 332.
      (c) Lin, M.-H.; Lin, W.-C.; Liu, H.-J.; Chuang, T.-H. J. Org. Chem. 2013, 78, 1278.

    7. [7]

      Liao, P.-H.; Bao, W.-L.; Zhang, Y.-M. Synth. Chem. 1997, 5, 374.

    8. [8]

    9. [9]

      (a) Naredla, R. R.; Klumpp, D. A. Chem. Rev. 2013, 113, 6905.
      (b) Nokami, T.; Yamane, Y.; Oshitani, S.; Kobayashi, J.-K, Matsui, S.-i.; Nishihara, T.; Uno, H.; Hayase, S.; Itoh, T. Org. Lett. 2015, 17, 3182.
      (c) Flagstad, T.; Petersen, M. T.; Nielsen, T. E. Angew. Chem., Int. Ed. 2015, 54, 8395.
      (d) Xiao, M.; Ren, D, Xu, L.; Li, S.-S.; Yu, L.; Xiao, J. Org. Lett. 2017, 19, 5724.
      (e) Hikawa, H.; Kotaki, F.; Kikkawa, S.; Azumaya, I. J. Org. Chem. 2019, 84, 1972.
      (f) Yu, H.; Lee, R.; Kim, H.; Lee, D. J. Org. Chem. 2019, 84, 3566.
      (g) Mayer, R. J.; Breugst, M.; Hampel, N.; Ofial, A. R.; Mayr, H. J. Org. Chem. 2019, 84, 8837.
      (h) Kinthada, L. K.; Medisetty, S. R.; Parida, A.; Babu, K. N.; Bisai, A. J. Org. Chem. 2017, 82, 8548.

    10. [10]

      Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452.  doi: 10.1021/jo9901337

    11. [11]

      Lebleu, T.; Paquin, J-F. Tetrahedron Lett. 2017, 58, 442.  doi: 10.1016/j.tetlet.2016.12.056

  • 加载中
    1. [1]

      Bolin Sun Jie Chen Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032

    2. [2]

      Yongxin LIUXingchen LIHongjia LIUDanni LITao ZHANGXi CHEN . Enhancement effect of Fe3O4 conversion to MIL-100(Fe) on activation of persulfate for degradation of antibiotic. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2503-2513. doi: 10.11862/CJIC.20250169

    3. [3]

      Ran YuChen HuRuili GuoRuonan LiuLixing XiaCenyu YangJianglan Shui . Catalytic Effect of H3PW12O40 on Hydrogen Storage of MgH2. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032

    4. [4]

      Tianhao GESirong LUZhiyin XIAOWei ZHONG . Synthesis of porphyrin-based ionic polymeric materials for catalytic application in CO2 conversion. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 722-736. doi: 10.11862/CJIC.20250312

    5. [5]

      Xiaogang Liu Mengyu Chen Yanyan Li Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007

    6. [6]

      Wenjuan SHIYuke LUXiuyuan LILei HOUYaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO2 adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220

    7. [7]

      Qingtao CHENXiangdong SHIXianghai RAOLiying JIANGChunxiao JIAFenghua CHEN . Catalytic and in situ surface-enhanced Raman scattering detection properties of graphene oxide/gold nanorod assembly. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 120-128. doi: 10.11862/CJIC.20250091

    8. [8]

      Ting YANGJia ANJinyu ZHANGRuonan FANRong YANXiaoxia JINGPanpan CHANGWei YAN . Synergistic enhancement of ion migration and sulfur conversion kinetics in lithium-sulfur batteries by CeO2/g-C3N4. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 519-530. doi: 10.11862/CJIC.20250274

    9. [9]

      Shiyan Cheng Yonghong Ruan Lei Gong Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

    10. [10]

      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

    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]

      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

    13. [13]

      Xinxin YUYongxing LIUXiaohong YIMiao CHANGFei WANGPeng WANGChongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438

    14. [14]

      Ning CHENJingle CHENHongyuan ZHUHuali CHENLiguang WUTing WANG . Mechanism and performance regulation of Co/Zr-doped mesoporous TiO2 catalysts in activating sodium persulfate for tetracycline degradation. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 507-518. doi: 10.11862/CJIC.20250275

    15. [15]

      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

    16. [16]

      Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018

    17. [17]

      Zhengyu ZhouHuiqin YaoYoulin WuTeng LiNoritatsu TsubakiZhiliang 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): 2312010-0. doi: 10.3866/PKU.WHXB202312010

    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]

      Qiuping Liu Yongxian Fan Wenxian Chen Mengdi Wang Mei Mei Genrong Qiang . Design of Ideological and Political Education for the Preparation Experiment of Ferrous Sulfate. University Chemistry, 2024, 39(2): 116-120. doi: 10.3866/PKU.DXHX202309083

    20. [20]

      Haozhe Hu Haoyu Zhang Changsheng Lu . Study on the Precipitation Process of Elemental Sulfur from the Decomposition Products of Thiosulfuric Acid: Is It an Unexpected Failed Experiment?. University Chemistry, 2025, 40(11): 409-415. doi: 10.12461/PKU.DXHX202412034

Metrics
  • PDF Downloads(7)
  • Abstract views(1775)
  • HTML views(148)

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