Visible-Light-Mediated Trifluoroalkylation of Isoquinolines via Three-Component Minisci-Type Reaction

被引:2
|
作者
Thakur, Ankita [1 ,2 ]
Gupta, Shiv Shankar [1 ,2 ]
Sharma, Upendra [1 ,2 ]
机构
[1] CSI IHBT, Chem Technol Div, C H Activat & Phytochemistry Lab, Palampur 176061, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
PHOTOREDOX; BONDS;
D O I
10.1021/acs.orglett.4c03096
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A sustainable photocatalytic approach has been established for trifluoroalkylation of isoquinoline via a three-component Minisci-type reaction using a green solvent. The polarity reversal radical cascade strategy renders the selective addition of an electrophilic CF3 radical to an olefin to forge a nucleophilic C-centered radical. This multicomponent approach is operationally simple and environmentally benign with various functional groups, viz. aldehydes, acetals, amides, and halides. Mechanistic investigations were carried out to elaborate the reductive quenching catalytic pathway.
引用
收藏
页码:8515 / 8520
页数:6
相关论文
共 50 条
  • [1] Visible-light-mediated three-component Minisci reaction for heteroarylethyl alcohols synthesis
    Dong, Jianyang
    Yue, Fuyang
    Liu, Jianhua
    Song, Hongjian
    Liu, Yuxiu
    Wang, Qingmin
    GREEN CHEMISTRY, 2021, 23 (20) : 7963 - 7968
  • [2] Visible-light-mediated photoredox decarbonylative Minisci-type alkylation with aldehydes under ambient air conditions
    Wang, Zhongzhen
    Ji, Xiaochen
    Zhao, Jinwu
    Huang, Huawen
    GREEN CHEMISTRY, 2019, 21 (20) : 5512 - 5516
  • [3] Visible-Light-Mediated Three-Component Cascade Sulfonylative Annulation
    Upreti, Ganesh Chandra
    Singh, Tavinder
    Ranjan, Sudhir
    Gupta, Raju Kumar
    Singh, Anand
    ACS OMEGA, 2022, 7 (34): : 29728 - 29733
  • [4] Three-Component Synthesis of β-Ketosulfonamides via Visible-Light-Mediated Generation of Sulfamoyl Radicals
    Hofman, Kamil
    Friedrich, Marius
    Manolikakes, Georg
    CHEMCATCHEM, 2025, 17 (06)
  • [5] Visible-Light-Mediated Three-Component Radical Iodosulfonylative Cyclization of Enynes
    Cheng, Qi
    Zhang, Fengrong
    Chen, Xiaoyun
    Han, Ying
    Yan, Chaoguo
    Shi, Yaocheng
    Hou, Hong
    Zhu, Shaoqun
    ORGANIC LETTERS, 2022, 24 (13) : 2515 - 2519
  • [6] Visible-Light-Mediated Three-Component Strategy for the Synthesis of Isoxazolines and Isoxazoles
    Li, Yanchuan
    Zhang, Yu
    Wang, Jinxin
    Xia, Dingding
    Zhuo, Miaomiao
    Zhu, Lu
    Li, Dong
    Ni, Shao-Fei
    Zhu, Yanping
    Zhang, Wei-Dong
    ORGANIC LETTERS, 2024, 26 (15) : 3130 - 3134
  • [7] Visible-Light-Mediated Vinyl-Thiophosphate Formation Via Three-Component Denitrative Cross-Coupling Reaction
    Huang, Xiao-Ying
    Zhu, Yu
    Ding, Zong-Cang
    Tang, Hai-Tao
    Pan, Ying-Ming
    Duan, Wen-Gui
    Cui, Fei-Hu
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (24) : 5015 - 5019
  • [8] Borylation of azines via a Minisci-type reaction
    Yang, Shengbiao
    Ye, Juntao
    CHEM, 2021, 7 (07): : 1703 - 1705
  • [9] Visible-Light-Mediated Deaminative Three-Component Dicarbofunctionalization of Styrenes with Benzylic Radicals
    Klauck, Felix J. R.
    Yoon, Hyung
    James, Michael J.
    Lautens, Mark
    Glorius, Frank
    ACS CATALYSIS, 2019, 9 (01) : 236 - 241
  • [10] Three-Component Minisci Reaction with 1,3-Dicarbonyl Compounds Induced by Visible Light
    Li, Tao
    Liang, Kangjiang
    Zhang, Yang
    Hu, Dongyan
    Ma, Zhixian
    Xia, Chengfeng
    ORGANIC LETTERS, 2020, 22 (06) : 2386 - 2390