Organic-Dye-Catalyzed Visible-Light-Mediated Alkoxycarbon-ylation of 2-Aryl-N-acryloyl Indoles with Carbazates

被引:2
|
作者
Du Changyuan [1 ]
Tang Yucai [1 ]
Duan Jinglin [1 ]
Yang Biyu [1 ]
He Yupeng [1 ]
Zhou Qian [1 ]
Liu Xuewen [1 ]
机构
[1] Hunan Univ Arts & Sci, Coll Chem & Mat Engn, Hunan Prov Engn Res Ctr Elect Wastewater Reuse Te, Hunan Prov Key Lab Water Treatment Funct Mat, Changde 415000, Hunan, Peoples R China
关键词
Rose Bengal; organic dye; visible-light; 2-aryl-indoles; indolo[2,1-a]isoquinolines; PHOTOREDOX CATALYSIS; BOND FORMATION; ARYLALKOXYCARBONYLATION; ESTERIFICATION; ALKENES; ESTERS; ACID;
D O I
10.6023/cjoc202305024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light-mediated organic dye photoredox-catalyzed alkoxycarbonylation of 2-aryl-N-acryloyl indoles to give valuable indolo[2,1-a]isoquinoline derivatives has been developed. With this approach, a variety of ester-substituted indolo[2,1-a]isoquinolines are prepared in moderate to good yields. Mild reaction conditions, metal free, visible light as a traceless energy source, economical and environmentally benign Rose Bengal as the catalyst, stable and easily accessible starting materials all make this methodology more attractive.
引用
收藏
页码:4268 / 4276
页数:9
相关论文
共 39 条
  • [1] Kinetics study of esterification of acetic acid with isobutanol in the presence of amberlite catalyst
    Altiokka, MR
    Çitak, A
    [J]. APPLIED CATALYSIS A-GENERAL, 2003, 239 (1-2) : 141 - 148
  • [2] Production of lactic acid esters catalyzed by heteropoly acid supported over ion-exchange resins
    Ayturk, E
    Hamamci, H
    Karakas, G
    [J]. GREEN CHEMISTRY, 2003, 5 (04) : 460 - 466
  • [3] Synthesis of Ester-Substituted Indolo[2,1-a]isoquinolines via Photocatalyzed Alkoxycarbonylation/Cyclization Reactions
    Chen, Jian-Qiang
    Tu, Xiaodong
    Qin, Binyan
    Huang, Shaoxin
    Zhang, Jun
    Wu, Jie
    [J]. ORGANIC LETTERS, 2022, 24 (02) : 642 - 647
  • [4] Efficient access to aliphatic esters by photocatalyzed alkoxycarbonylation of alkenes with alkyloxalyl chlorides
    Chen, Jian-Qiang
    Tu, Xiaodong
    Tang, Qi
    Li, Ke
    Xu, Liang
    Wang, Siyu
    Ji, Mingjuan
    Li, Zhiming
    Wu, Jie
    [J]. NATURE COMMUNICATIONS, 2021, 12 (01)
  • [5] Aerobic Oxidative Cascade Thiolation and Cyclization to Construct Indole-Fused Isoquinolin-6(5H)-one Derivatives in EtOH
    Cui, Huanhuan
    Niu, Changhao
    Zhang, Chun
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 15835 - 15844
  • [6] Visible Light Photocatalysis: Applications and New Disconnections in the Synthesis of Pharmaceutical Agents
    Douglas, James J.
    Sevrin, Martin J.
    Stephenson, Corey R. J.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (07) : 1134 - 1147
  • [7] Alkyl Carbazates for Electrochemical Deoxygenative Functionalization of Heteroarenes
    Gao, Yongyuan
    Wu, Zhengguang
    Yu, Lei
    Wang, Yi
    Pan, Yi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (27) : 10859 - 10863
  • [8] Iron-Catalyzed Regioselective Alkoxycarbonylation of Imidazoheterocycles with Carbazates
    Gao, Yongyuan
    Lu, Weiye
    Liu, Ping
    Sun, Peipei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06): : 2482 - 2487
  • [9] Hao R., 2022, ASIAN J ORG CHEM, V11, pe202100766, DOI DOI 10.1002/ajoc.202100766
  • [10] Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides
    Jiang, Shuai-Shuai
    Xiao, Yu-Ting
    Wu, Yan-Chen
    Luo, Shu-Zheng
    Song, Ren-Jie
    Li, Jin-Heng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (25) : 4843 - 4847