Visible light photocatalytic cross-coupling and addition reactions of arylalkynes with perfluoroalkyl iodides

被引:20
|
作者
Xiao, Yelan [1 ]
Chun, Yuen-Kiu [1 ]
Cheng, Shun-Cheung [1 ]
Liu, Ruoyang [1 ]
Tse, Man-Kit [1 ]
Ko, Chi-Chiu [1 ]
机构
[1] City Univ Hong Kong, Dept Chem, Kowloon Tong, Tat Chee Ave, Hong Kong, Peoples R China
关键词
TRANSITION-METAL-COMPLEXES; TRANSFER RADICAL-ADDITION; STEREOSELECTIVE CARBOPERFLUOROALKYLATION; PHOTOREDOX CATALYSIS; ALKYNES; DIFLUOROALKYLATION; TRIFLUOROMETHYLATION; FLUOROALKYLATION; ALKENES; IODOPERFLUOROALKYLATION;
D O I
10.1039/d0ob01767a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible light photocatalytic cross-coupling and addition reactions of arylalkynes with perfluoroalkyl iodides have been developed. Through slight modifications of the reaction conditions, reactions that are selective for the preparation of the C-C coupling product (perfluoroalkyl alkynes) and the addition products (iodo-perfluoroalkyl substituted alkenes) can be achieved. These reactions work well with different types of alkynes and perfluoroalkyl iodides. As the iodide generated from the reaction can serve as a reductant to regenerate the photocatalyst from its oxidized form, no sacrificial electron donor is required.
引用
收藏
页码:8686 / 8693
页数:8
相关论文
共 50 条
  • [31] Visible-light promoted cross-coupling of ethyl iododifluoroacetate with silyl enol ethers for the synthesis of ?-fluoroenones via noncovalent interactions
    Huang, Qi-Ping
    Li, Wei-Piao
    Li, Rui
    Zhao, Liang
    Wang, Hao-Yang
    Li, Xuefei
    Wang, Pan
    He, Chun-Yang
    TETRAHEDRON LETTERS, 2022, 97
  • [32] Electroreductive Cross-Coupling Reactions: Carboxylation, Deuteration, and Alkylation
    Li, Pengfei
    Wang, Yanwei
    Zhao, Hanying
    Qiu, Youai
    ACCOUNTS OF CHEMICAL RESEARCH, 2024, 58 (01) : 113 - 129
  • [33] Cross-Coupling Reactions of Persistent Tertiary Carbon Radicals
    Sohtome, Yoshihiro
    Kanomata, Kyohei
    Sodeoka, Mikiko
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2021, 94 (03) : 1066 - 1079
  • [34] Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions
    Yuan, Yong
    Lei, Aiwen
    ACCOUNTS OF CHEMICAL RESEARCH, 2019, 52 (12) : 3309 - 3324
  • [35] Synthesis of HIV NNRTI Doravirine Analogues via Visible-Light Photoredox Decarboxylative Cross-Coupling
    Suen, Linda M.
    Wang, Cheng
    Hunter, David N.
    Mitchell, Helen J.
    Converso, Antonella
    ElMarrouni, Abdellatif
    SYNTHESIS-STUTTGART, 2018, 50 (16): : 3177 - 3186
  • [36] Dehydrative Cross-Coupling Reactions of Allylic Alcohols with Olefins
    Gumrukcu, Yasemin
    de Bruin, Bas
    Reek, Joost N. H.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (35) : 10905 - 10909
  • [37] Visible light-induced aerobic oxidative cross-coupling reaction: preparation of α-indolyl glycine derivatives
    Ni, Cheng
    Chen, Wei
    Jiang, Chunhui
    Lu, Hongfei
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (02) : 313 - 316
  • [38] Visible Light Catalyzed Reductive Cross-Coupling of α-CF3-alkyl Bromide and Alkynyl Bromide
    Tian, Yiqiang
    Li, Yi
    Zhang, Chun
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (20) : 2479 - 2484
  • [39] Visible-Light-Promoted C-S Cross-Coupling via Intermolecular Charge Transfer
    Liu, Bin
    Lim, Chern-Hooi
    Miyake, Garret M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (39) : 13616 - 13619
  • [40] Asymmetric Radical-Radical Cross-Coupling through Visible-Light-Activated Iridium Catalysis
    Wang, Chuanyong
    Qin, Jie
    Shen, Xiaodong
    Riedel, Radostan
    Harms, Klaus
    Meggers, Eric
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (02) : 685 - 688