CuCl2-Catalyzed α-Chloroketonation of Aromatic Alkenes via Visible-Light-Induced LMCT

被引：6
|
作者：
He, Xing-Xian [1 ]
Chang, Huan-Huan [1 ]
Zhao, Ying-Xue [1 ]
Li, Xiang-Jie [1 ]
Liu, Sheng-An [1 ]
Zang, Zhong-Lin [1 ]
Zhou, Cheng-He [1 ]
Cai, Gui-Xin [1 ]
机构：
[1] Southwest Univ, Inst Bioorgan & Med Chem, Sch Chem & Chem Engn, Key Lab Qual & Safety Control Citrus Fruits,Minis, Chongqing 400715, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2023年 / 18卷 / 01期
关键词：
aromatic alkenes; alpha-chloroketones; CuCl2; LMCT; photocatalysis; C-H BOND; N-BROMOSUCCINIMIDE; AMMONIUM-CHLORIDE; METAL-FREE; KETONES; CHLORINATION; MILD; BROMINATION; ALKYNES; REACTIVITY;
D O I：
10.1002/asia.202200954
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Here we report a copper-catalyzed protocol for the synthesis of alpha-chloroketones from aromatic alkenes including electron-deficient olefins under visible-light irradiation. Preliminary mechanistic studies show that the peroxo Cu(II) species is the key intermediate and hydroperoxyl (HOO.) and chlorine (Cl.) radicals can be generated by ligand-to-metal charge transfer (LMCT).
引用
收藏
页数：5
相关论文
共 50 条
  • [1] Visible-Light-Induced Vicinal Dichlorination of Alkenes through LMCT Excitation of CuCl2
    Lian, Pengcheng
    Long, Wenhao
    Li, Jingjing
    Zheng, Yonggao
    Wan, Xiaobing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (52) : 23603 - 23608
  • [2] Visible-light-induced hydroalkylation of alkenes with aromatic β-ketoesters
    Gong, Ming
    Li, Qingrui
    Qin, Honghong
    Fu, Haixin
    Li, Guoping
    Li, Yabo
    Wu, Yangjie
    CHEMICAL COMMUNICATIONS, 2024, 60 (98) : 14664 - 14667
  • [3] Visible-light-induced controllable ?-chlorination of nafimidone derivatives through LMCT excitation of CuCl2
    Shen, Jiabin
    Wang, Zhihao
    Shen, Chao
    Zhang, Pengfei
    MOLECULAR CATALYSIS, 2023, 537
  • [4] Visible-Light-Induced Aminochlorination of Alkenes
    Mejri, Emna
    Higashida, Kosuke
    Kondo, Yuta
    Nawachi, Anna
    Morimoto, Hiroyuki
    Ohshima, Takashi
    Sawamura, Masaya
    Shimizu, Yohei
    ORGANIC LETTERS, 2023, 25 (24) : 4581 - 4585
  • [5] Visible-Light-Induced Copper-Catalyzed Alkynylation/Alkylation of Alkenes
    Zhang, Yajing
    Zhang, Dayong
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05): : 3213 - 3223
  • [6] Effective Au(III)-CuCl2-catalyzed addition of alcohols to alkenes
    Zhang, Xin
    Corma, Avelino
    CHEMICAL COMMUNICATIONS, 2007, (29) : 3080 - 3082
  • [7] 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
  • [8] Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes
    Xiong, Yang
    Zhang, Guozhu
    ORGANIC LETTERS, 2019, 21 (19) : 7873 - 7877
  • [9] Visible-light-induced intermolecular aminoselenation of alkenes
    Liu, Gong-Qing
    Zhou, Chen-Fan
    Zhang, Yun-Qian
    Yi, Wei
    Wang, Peng-Fei
    Liu, Ji
    Ling, Yong
    GREEN CHEMISTRY, 2021, 23 (24) : 9968 - 9973
  • [10] Visible-light-induced radical hydrodifluoromethylation of alkenes
    Yu, Jiao
    Lin, Jin-Hong
    Cao, Yu-Cai
    Xiao, Ji-Chang
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (20) : 3580 - 3583
12345