Visible Light-Induced Organophotoredox-Catalyzed β-Hydroxytrifluoromethylation of Unactivated Alkenes

被引:0
|
作者
Behera, Mousumi [1 ]
Dharpure, Pankaj D. [1 ]
Sahu, Ajit K. [1 ]
Bhat, Ramakrishna G. [1 ]
机构
[1] Indian Inst Sci Educ & Res IISER Pune, Dept Chem, Pune 411008, Maharashtra, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期
关键词
PHOTOREDOX CATALYSIS; TRIFLUOROMETHYLATION REACTIONS; OXYTRIFLUOROMETHYLATION; DIFUNCTIONALIZATION; CHEMISTRY; FLUORINE;
D O I
10.1021/acs.joc.4c00967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a mild transition metal-free organophotoredox-catalyzed approach for beta-hydroxytrifluoromethylation of unactivated alkenes using CF3SO2Na and acridinium salt. The protocol is compatible with various mono-, di-, and trisubstituted aliphatic unactivated alkenes containing numerous functional groups and natural product derivatives. Further, the postsynthetic modifications of the synthesized trifluoromethylated products have been demonstrated through cross-coupling and functional group interconversion reactions. The method proved to be scalable and it works smoothly under the direct exposure of sunlight. A plausible mechanism has been proposed based on the fluorescence quenching experiment and cyclic voltammetry analysis.
引用
收藏
页码:14695 / 14709
页数:15
相关论文
共 50 条
  • [1] Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes
    Gupta, Subham
    Kundu, Abhishek
    Ghosh, Sumit
    Chakraborty, Amrita
    Hajra, Alakananda
    GREEN CHEMISTRY, 2023, 25 (21) : 8459 - 8493
  • [2] Organophotoredox-Catalyzed Reductive Tetrafluoroalkylation of Alkenes
    Kostromitin, Vladislav S.
    Levin, Vitalij V.
    Dilman, Alexander D.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (10): : 6523 - 6531
  • [3] Visible light-induced perfluoroalkylative carbonylation of unactivated alkenes
    Zhang, Youcan
    Yuan, Yang
    Geng, Hui-Qing
    Xu, Jian-Xing
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2022, 413 : 214 - 220
  • [4] Visible light induced hydrophosphinylation of unactivated alkenes catalyzed by salicylaldehyde
    Yuan, Zeqin
    Wang, Simin
    Li, Miaomiao
    Chen, Tian
    Fan, Jiaye
    Xiong, Fuying
    Li, Qianggen
    Hu, Ping
    Wang, Bi-Qin
    Cao, Peng
    Li, Yang
    GREEN CHEMISTRY, 2021, 23 (10) : 3600 - 3606
  • [5] Visible-Light Organophotoredox-Catalyzed Synthesis of Precursors for Horner-Type Olefinations
    Nebe, Marco M.
    Loeper, Daniel
    Fuermeyer, Fabian
    Opatz, Till
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (20-21) : 2471 - 2476
  • [6] Visible-Light Organophotoredox-Catalyzed Phosphonoalkylation of Alkenes via Deaminative Three-Component Radical-Radical Coupling
    Das, Subhodeep
    Banerjee, Amit
    Das, Pritha
    Jana, Ranjan
    SYNLETT, 2024, 35 (20) : 2471 - 2476
  • [7] Visible-Light-Induced Organophotoredox-Catalyzed Phosphonylation of 2H-Indazoles with Diphenylphosphine Oxide
    Singsardar, Mukta
    Dey, Amrita
    Sarkar, Rajib
    Hajra, Alakananda
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12694 - 12701
  • [8] Synthesis of β-fluorocarboxylic esters via organophotoredox-catalyzed fluoroalkoxycarbonylation of alkenes in EtOH
    Wang, Xinhua
    Chen, Yi
    Liang, Ping
    Chen, Jian-Qiang
    Wu, Jie
    GREEN CHEMISTRY, 2022, 24 (13) : 5077 - 5082
  • [9] Visible-Light-Induced Iminothiolation of Unactivated Alkenes
    Wang, Ding-Xing
    Cai, Sai-Hu
    Liu, Haidong
    Ye, Lu
    Zhu, Chuan
    Feng, Chao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1386 - 1389
  • [10] Visible Light-Induced Radical Iodoperfluoroalkylation of Unactivated Olefins Cooperatively Catalyzed by Enamines and Amines
    Yajima, Tomoko
    Murase, Mao
    Ofuji, Yu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (25) : 3808 - 3811