A new approach to access difluoroalkylated diarylmethanes via visible-light photocatalytic cross-coupling reactions

被引:69
|
作者
Zhao, Yin-Na [1 ]
Luo, Yong-Chun [1 ]
Wang, Zhu-Yin [1 ]
Xu, Peng-Fei [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
关键词
PARA-QUINONE METHIDES; ARYL BORONIC ACIDS; ASYMMETRIC 1,6-CONJUGATE ADDITION; PHOTOREDOX CATALYSIS; ALPHA-ALKYLATION; EXPEDIENT ACCESS; PALLADIUM; RADICALS; ALDEHYDES; ARENES;
D O I
10.1039/c8cc01486h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Difluoroalkylated diarylmethanes with biological and pharmacological potentials were synthesized from para-quinone methides (p-QMs) and difluoroalkylating reagents via a visible light photocatalysis strategy. Mechanism studies showed that the excited photocatalyst, *fac-Ir(ppy)(3), was primarily quenched by p-QMs and the generated diarylmethane radical intermediates then underwent a radical-radical cross-coupling reaction with difluoroalkyl radicals. This reaction features mild conditions, high efficiency and wide functional group compatibility.
引用
收藏
页码:3993 / 3996
页数:4
相关论文
共 50 条
  • [1] An Efficient Approach to Access 2,2-Diarylanilines via Visible-Light-Promoted Decarboxylative Cross-Coupling Reactions
    Luo, Cong
    Zhou, Tongyao
    Wang, Wei
    Han, Pan
    Jing, Linhai
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (09) : 2342 - 2346
  • [2] Visible light photocatalytic cross-coupling and addition reactions of arylalkynes with perfluoroalkyl iodides
    Xiao, Yelan
    Chun, Yuen-Kiu
    Cheng, Shun-Cheung
    Liu, Ruoyang
    Tse, Man-Kit
    Ko, Chi-Chiu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (42) : 8686 - 8693
  • [3] Visible Light Induced Cross-Coupling Hydrogen Evolution Reactions
    Zhong Jian-Ji
    Meng Qing-Yuan
    Chen Bin
    Tung Chen-Ho
    Wu Li-Zhu
    ACTA CHIMICA SINICA, 2017, 75 (01) : 34 - 40
  • [4] Synthesis of Thioamides via Decarboxylative/Oxidative Cross-Coupling Reaction by Visible-Light Photocatalysis
    Sarkar, Subhankar
    Pal, Satyajit
    Santra, Sougata
    Zyryanov, Grigory V.
    Ghosh, Susanta
    Majee, Adinath
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (06)
  • [5] 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
  • [6] Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis
    Akram, Manjur O.
    Mali, Pramod S.
    Patil, Nitin T.
    ORGANIC LETTERS, 2017, 19 (12) : 3075 - 3078
  • [7] Metal-Free Synthesis of Diarylmethanes through Visible-Light Induced Radical Reactions with Arylamines
    Wang, Youjia
    Duan, Ruochen
    Wu, Yanhui
    Li, Xulian
    Deng, Chao
    CHEMISTRYSELECT, 2021, 6 (24): : 6097 - 6101
  • [8] Heterogeneous Photocatalyzed C-C Cross-coupling Reactions Under Visible-light and Near-infrared Light Irradiation
    Gu, Quan
    Jia, Qiaohui
    Long, Jinlin
    Gao, Ziwei
    CHEMCATCHEM, 2019, 11 (02) : 669 - 683
  • [9] Visible Light Driven Photocatalytic Cross-Coupling Reactions on Nano Pd/ZnO Photocatalyst at Room-Temperature
    Hosseini-Sarvari, Mona
    Bazyar, Zahra
    CHEMISTRYSELECT, 2018, 3 (06): : 1898 - 1907
  • [10] Cross-Coupling of Carbonyl Derivatives and N-Arylamines Enabled by Visible Light for Easy Access to 1,2-Amino Alcohols
    Xu, Yan
    Zhuang, Haohuan
    Song, Yulin
    Shi, Weiqiong
    Chen, Xu
    Zhang, Lixiang
    Huang, Xuan
    Zhang, Junmin
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (02): : 1078 - 1084