Hydrodifluoromethylation of unactivated alkenes enabled by Visible-Light Photocatalysis

被引:2
作者
Jha, Avishek Kumar [1 ]
Kumar, Vivek [1 ]
Perumandla, Sanjay Kumar [1 ]
Yatham, Veera Reddy [1 ]
机构
[1] Indian Inst Sci Educ & Res, Sch Chem, Thiruvananthapuram IISER TVM, Thiruvananthapuram 695551, Kerala, India
关键词
visible-light; alkenes; radical; difluoromethylation; PHOTOREDOX CATALYSIS; DIFLUOROMETHYLATION;
D O I
10.1002/cptc.202300288
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In the present manuscript, we have reported a general catalytic strategy that allows the synthesis of a variety of difluoro methylated alkanes from the corresponding unactivated alkenes using commercially available radical difluoromethylating reagent (CF2HSO2Na) under visible light photocatalysis. Further, this strategy allows the late-stage modification of various alkenes derived from pharmaceutically relevant drugs. Photocatalytic hydro-difluoromethylaton of unactivated alkenes has been developed using a commercially available difluoromethylating reagent (CF2HSO2Na). This methodology tolerates a variety of functional groups and allows late-stage modification of various alkenes derived from pharmaceutically relevant drugs. image
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Thiosulfonylation of Unactivated Alkenes with Visible-Light Organic Photocatalysis
    Gadde, Karthik
    Mampuys, Pieter
    Guidetti, Andrea
    Ching, H. Y. Vincent
    Herrebout, Wouter A.
    Van Doorslaer, Sabine
    Tehrani, Kourosch Abbaspour
    Maes, Bert U. W.
    ACS CATALYSIS, 2020, 10 (15): : 8765 - 8779
  • [2] Visible-Light-Induced Hydrodifluoromethylation of Unactivated Alkenes with Difluoroacetic Anhydride
    Zhu, Xiaoliang
    Zhang, Min
    Shen, Lujie
    Su, Weiping
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12) : 8828 - 8835
  • [3] Hydrophosphinylation of unactivated alkenes with secondary phosphine oxides under visible-light photocatalysis
    Yoo, Woo-Jin
    Kobayashi, Shu
    GREEN CHEMISTRY, 2013, 15 (07) : 1844 - 1848
  • [4] Deracemization Enabled by Visible-Light Photocatalysis
    Shi, Qinglong
    Ye, Juntao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (13) : 4998 - 5001
  • [5] Atom-Transfer Radical Addition to Unactivated Alkenes by using Heterogeneous Visible-Light Photocatalysis
    Mao, Liang-Liang
    Cong, Huan
    CHEMSUSCHEM, 2017, 10 (22) : 4461 - 4464
  • [6] Visible-light photoredox catalysis enabled bromination of phenols and alkenes
    Zhao, Yating
    Li, Zhe
    Yang, Chao
    Lin, Run
    Xia, Wujiong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 622 - 627
  • [7] Visible-Light-Induced Hydrodifluoromethylation of Alkenes with a Bromodifluoromethylphosphonium Bromide
    Lin, Qing-Yu
    Xu, Xiu-Hua
    Zhang, Ke
    Qing, Feng-Ling
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) : 1479 - 1483
  • [8] Bioorthogonal Synthetic Chemistry Enabled by Visible-Light Photocatalysis
    Mato, Mauro
    Fernandez-Gonzalez, Xulian
    DAvino, Cinzia
    Tomas-Gamasa, Maria
    Mascarenas, Jose L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (47)
  • [9] Distal Functional Group Migration for Visible-light Induced Carbo-difluoroalkylation/monofluoroalkylation of Unactivated Alkenes
    Yu, Jiajia
    Wang, Dongping
    Xu, Yan
    Wu, Zhen
    Zhu, Chen
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (04) : 744 - 750
  • [10] Visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide
    Hu, Wei-Qiang
    Xu, Xiu-Hua
    Qing, Feng-Ling
    JOURNAL OF FLUORINE CHEMISTRY, 2018, 208 : 73 - 79