Citation: LI Jie, LIU Yilin, DENG Youlin, WANG Wenxin, WANG Shuowen, LI Zengzeng, TANG Shi. Visible-Light-Induced Cyclization of Alkenes to Form Difluoroacetating Isoquinolinedione[J]. Chinese Journal of Applied Chemistry, ;2016, 33(6): 677-684. doi: 10.11944/j.issn.1000-0518.2016.06.150316 shu

Visible-Light-Induced Cyclization of Alkenes to Form Difluoroacetating Isoquinolinedione

  • Corresponding author: LIU Yilin,  TANG Shi, 
  • Received Date: 31 August 2015
    Available Online: 23 December 2015

    Fund Project:

  • A visible-light-induced cyclization reaction of activated alkenes leading to difluoroacetating isoquinolinedione was developed. By visible-light photoredox catalysis, various N-alkyl-N-methacryloyl benzamides underwent radical cascade cyclization smoothly and afforded a series of difluoroacetating isoquinolinediones in 66%~75% yields, providing a highly efficient, mild means to fluorinated isoquinolinediones with potential bioactivity.
  • 加载中
    1. [1]

      [1] Purser S,Moore P R,Swallow S,et al.Fluorine in Medicinal Chemistry[J].Chem Soc Rev,2008,37(2):320-330.

    2. [2]

      [2] Prakash G S,Chacko S.Novel Nucleophilic and Electrophilic Fluoroalkylation Methods[J].Curr Opin Drug Discovery Dev,2008,11(6):793-802.

    3. [3]

      [3] Chen Y H,Zhang Y H,Zhang H J,et al.Design,Synthesis,and Biological Evaluation of Isoquino Line-1,3,4-trione Derivatives as Potent Caspase-3 Inhibitors[J].J Med Chem,2006,49(5):1613-1623.

    4. [4]

      [4] Braña M F,Castellano J M,Perron D,et al.Chromophore-Modified Bis-Naphthalimides:Synthesis and Antitumor Activity of Bis-Dibenz[de,h]isoquinoline-1,3-diones[J].J Med Chem,1997,40(4):449-454.

    5. [5]

      [5] Quiclet-Sire B,Zard S Z.An Expedient Synthesis of Homophthalimides[J].Chem Commun,2002,34(20):2306-2307.

    6. [6]

      [6] TANG Yucai,ZHANG Min,LI Xiaoqing,et al.Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes:Synthesis of Isoquinolinedione Derivatives[J].Chinese J Org Chem,2015,35(4):875-881(in Chinese).唐裕才,张敏,李小青,等.四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物[J].有机化学,2015,35(4):875-881.

    7. [7]

      [7] Liu Q,Chu L,Qing F L.Direct Introduction of Ethoxylcarbonyldifluoromethyl-group to Heteroarenes with Ethyl Bromodifluoroacetate via Visible-Light Photocatalysis[J].Chem J Org,2013,31(7):885-891.

    8. [8]

      [8] Fu W,Zhu M,Zou G,et al.Visible-Light-Mediated Radical Aryldifluoroacetylation of N-Arylacrylamides to Give Difluoroacetylated Oxindoles[J].Asian J Org Chem,2014,3(12):1273-1276.

    9. [9]

      [9] Fu W,Zhu M,Zou G,et al.Visible-Light-Mediated Radical Aryldifluoroacetylation of Alkynes with Ethyl Bromodifluoroacetate for the Synthesis of 3-Difluoroacetylated Coumarins[J].J Org Chem,2015,80(9):4766-4770.

    10. [10]

      [10] Wang Y,Qiu J,Kong D,et al.Silver-Mediated Radical Trifluoromethylarylation of Activated Alkenes for the Synthesis of Oxindoles Bearing a CF3 Group[J].Synlett,2014,25(12):1731-1734.

    11. [11]

      [11] Xu P,Hu K,G Z,et al.Visible Light Promoted Carbodifluoroalkylation of Allylic Alcohols via Concomitant 1,2-Aryl Migration[J].Chem Commun,2015,51(33):7222-7225.

    12. [12]

      [12] Tang S,Li Z H,Wang M W,et al.Metal-free Cascade Cyclization of Alkenes Toward Perfluorinated Oxindoles[J].Org Biomol Chem,2015,13(3):5285-5288.

    13. [13]

      [13] ZHOU Dong,LI Yuhua,DENG Youlin,et al.Recent Progress on Radical C-H Bond Cyclization to Form Oxindoles[J].J Jishou Univ(Nat Sci Ed),2015,36(2):60-70(in Chinese).周栋,李玉花,邓佑林,等.自由基介导C-H键环化合成吲哚酮的研究进展[J].吉首大学学报(自然科学版),2015,36(2):60-70.

    14. [14]

      [14] Wang Q K,Maria C,Noelia F,et al.Metal-Free Aryltrifluoromethylation of Activated Alkenes[J].Angew Chem Int Ed,2013,52(49):13086-13090.

    15. [15]

      [15] Zhang L,Yang C,Xu Z,et al.Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions[J].J Org Chem,2015,80(49):5730-5736.

    16. [16]

      [16] Zhang M,Xie P,Zhao W,et al.Cascade Couplings of N-Alkyl-N-methacryloyl Benzamides with Ethers and Benzenesulfonohydrazides to Generate Isoquinoline-1,3(2H,4H)-dione Derivatives[J].J Org Chem,2015,80(8):4176-4183.

    17. [17]

      [17] Zhang L,Yang C,Xu Z,et al.Difunctionalization of Alkenes via the Visible-Light-Induced Trifluoromethylarylation/1,4-Aryl Shift/Desulfonylation Cascade Reactions[J].J Org Chem,2015,80(11):5730-5736.

  • 加载中
    1. [1]

      Jie Li Huida Qian Deyang Pan Wenjing Wang Daliang Zhu Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076

    2. [2]

      Yurong Tang Yunren Shi Yi Xu Bo Qin Yanqin Xu Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087

    3. [3]

      Juntao YanLiang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-0. doi: 10.3866/PKU.WHXB202312024

    4. [4]

      Zhiquan ZhangBaker RhimiZheyang LiuMin ZhouGuowei DengWei WeiLiang MaoHuaming LiZhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO2 Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029

    5. [5]

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

    6. [6]

      Lewang YuanYaoyao PengZong-Jie GuanYu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086

    7. [7]

      Bo YANGGongxuan LÜJiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346

    8. [8]

      Xinzhe HUANGLihui XUYue YANGLiming WANGZhangyong LIUZhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO4/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212

    9. [9]

      Bing LIUHuang ZHANGHongliang HANChangwen HUYinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398

    10. [10]

      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

    11. [11]

      Qin LiHuihui ZhangHuajun GuYuanyuan CuiRuihua GaoWei-Lin DaiIn situ Growth of Cd0.5Zn0.5S Nanorods on Ti3C2 MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-0. doi: 10.3866/PKU.WHXB202402016

    12. [12]

      Yuanqing WangYusong PanHongwu ZhuYanlei XiangRong HanRun HuangChao DuChengling Pan . Enhanced Catalytic Activity of Bi2WO6 for Organic Pollutants Degradation under the Synergism between Advanced Oxidative Processes and Visible Light Irradiation. Acta Physico-Chimica Sinica, 2024, 40(4): 2304050-0. doi: 10.3866/PKU.WHXB202304050

    13. [13]

      Fangxuan LiuZiyan LiuGuowei ZhouTingting GaoWenyu LiuBin Sun . 中空结构光催化剂. Acta Physico-Chimica Sinica, 2025, 41(7): 100071-0. doi: 10.1016/j.actphy.2025.100071

    14. [14]

      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

    15. [15]

      Hailang JIAPengcheng JIHongcheng LI . Preparation and performance of nickel doped ruthenium dioxide electrocatalyst for oxygen evolution. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1632-1640. doi: 10.11862/CJIC.20240398

    16. [16]

      Xuefei Zhao Xuhong Hu Zhenhua Jia . 理论与计算化学在傅-克烷基化反应教学中的应用. University Chemistry, 2025, 40(8): 360-367. doi: 10.12461/PKU.DXHX202410008

    17. [17]

      Huiwei DingBo PengZhihao WangQiaofeng Han . Advances in Metal or Nonmetal Modification of Bismuth-Based Photocatalysts. Acta Physico-Chimica Sinica, 2024, 40(4): 2305048-0. doi: 10.3866/PKU.WHXB202305048

    18. [18]

      Yushan CaiFang-Xing Xiao . Revisiting MXenes-based Photocatalysis Landscape: Progress, Challenges, and Future Perspectives. Acta Physico-Chimica Sinica, 2024, 40(8): 2306048-0. doi: 10.3866/PKU.WHXB202306048

    19. [19]

      Yuanyin CuiJinfeng ZhangHailiang ChuLixian SunKai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-0. doi: 10.3866/PKU.WHXB202405016

    20. [20]

      Yu LiuPengfei LiYize LiuZaicheng Sun . Recent advances in carbon dots as a single photocatalyst. Acta Physico-Chimica Sinica, 2026, 42(2): 100167-0. doi: 10.1016/j.actphy.2025.100167

Metrics
  • PDF Downloads(0)
  • Abstract views(704)
  • HTML views(74)

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