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

LI Jie ^a ,
LIU Yilin ^b,, ,
DENG Youlin ^a ,
WANG Wenxin ^a ,
WANG Shuowen ^a ,
LI Zengzeng ^a ,
TANG Shi ^a,,

1.
a College of Chemistry and Chemical Engineering, Jishou University, Jishou, Hu'nan 427000, China;
2.
b Huaihua Key Laboratory of Functional Inorganic & Polymeric Materials, Huaihua University, Huaihua, Hu'nan 418008, China

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.
- visible-light-induced,
- difluoroacetating,
- Ir photocatalyst,
- isoquinolinedione
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.
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 Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
4. [4]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
5. [5]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei 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
6. [6]
  Bo YANG , Gongxuan LÜ , Jiantai 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
7. [7]
  Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian 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
8. [8]
  Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd_0.5Zn_0.5S Nanorods on Ti₃C₂ MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-. doi: 10.3866/PKU.WHXB202402016
9. [9]
  Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
10. [10]
  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
11. [11]
  Asif Hassan Raza , Shumail Farhan , Zhixian Yu , Yan Wu . 用于高效制氢的双S型ZnS/ZnO/CdS异质结构光催化剂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406020-. doi: 10.3866/PKU.WHXB202406020
12. [12]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
13. [13]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
14. [14]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
15. [15]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
16. [16]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
17. [17]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
18. [18]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
19. [19]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
20. [20]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(438)
HTML views(57)

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