Visible Light-Induced Hydroxyalkylation of Heteroarenes with Aliphatic Alcohols

被引:4
|
作者
Xu Dongping [1 ]
Huang Fei [1 ]
Tang Lin [1 ]
Zhang Xinming [1 ]
Zhang Wu [1 ]
机构
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Wuhu 241000, Anhui, Peoples R China
关键词
alcohol; cross-dehydrogenative coupling; heteroarene; hydroxyalkylation; visible light-induction; C-H FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; AMINATION REACTIONS; CARBOXYLIC-ACIDS; METAL; ETHERS; C(SP(3))-H; QUINOXALIN-2(1H)-ONES; HETEROARYLATION; AMINES;
D O I
10.6023/cjoc202112032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient visible light-induced direct cross-dehydrogenative coupling of heteroarenes with aliphatic alcohols in aqueous solution at ambient temperature was developed. The reaction is initiated by persulfate salts and does not require the use of stoichiometric acid for activation of the heterocycle. alpha-Hydroxyalkyl radicals transiently generated from alcohols via hydrogen atom transfer (HAT) undergo Minisci-type reactions with a range of heteroarenes. This protocol was highlighted by photocatalyst-free, green solvent, mild conditions, readily available starting materials, and wide functional group tolerance.
引用
收藏
页码:1493 / 1500
页数:8
相关论文
共 54 条
  • [1] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis
    Beatty, Joel W.
    Stephenson, Corey R. J.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) : 1474 - 1484
  • [2] Catalytic Asymmetric 1,4-Reduction of α-Branched 2-Vinyl-azaarenes by a Chiral SPINOL-Derived Borophosphate
    Cao, Yang
    Zhang, Shouqi
    Antilla, Jon C.
    [J]. ACS CATALYSIS, 2020, 10 (19): : 10914 - 10919
  • [3] Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings
    Chen, Bin
    Wu, Li-Zhu
    Tung, Chen-Ho
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (10) : 2512 - 2523
  • [4] Site-specific hydroxyalkylation of chromones via alcohol mediated Minisci-type radical conjugate addition
    Chen, Rongzhen
    Yu, Jin-Tao
    Cheng, Jiang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (11) : 1823 - 1827
  • [5] Palladium-Catalyzed Minisci Reaction with Simple Alcohols
    Correia, Camille A.
    Yang, Luo
    Li, Chao-Jun
    [J]. ORGANIC LETTERS, 2011, 13 (17) : 4581 - 4583
  • [6] Visible light-promoted C-H functionalization of ethers and electron-deficient arenes
    Devari, Shekaraiah
    Shah, Bhahwal Ali
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (07) : 1490 - 1493
  • [7] Recent Advances in Visible-Light-Mediated Minisci Reactions
    Dong, Jianyang
    Liu, Yuxiu
    Wang, Qingmin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (10) : 3771 - 3791
  • [8] Beyond Friedel and Crafts: Innate Alkylation of C-H Bonds in Arenes
    Evano, Gwilherm
    Theunissen, Cedric
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (23) : 7558 - 7598
  • [9] Copper-catalyzed oxidative coupling of quinoxalin-2(1H)-ones with alcohols: access to hydroxyalkylation of quinoxalin-2(1H)-ones
    Fu, Junhao
    Yuan, Jinwei
    Zhang, Yue
    Xiao, Yongmei
    Mao, Pu
    Diao, Xiaoqiong
    Qu, Lingbo
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (23): : 3382 - 3390
  • [10] Photocatalytic redox-neutral hydroxyalkylation of N-heteroaromatics with aldehydes
    Fuse, Hiromu
    Nakao, Hiroyasu
    Saga, Yutaka
    Fukatsu, Arisa
    Kondo, Mio
    Masaoka, Shigeyuki
    Mitsunuma, Harunobu
    Kanai, Motomu
    [J]. CHEMICAL SCIENCE, 2020, 11 (44) : 12206 - 12211