Visible Light-Induced Three-Component Alkoxyalkylation of Alkenes with α-Halocarbonyls and Alcohols

被引:0
|
作者
Chowdhury, Soumyadeep Roy [2 ]
Kim, Hun Young [1 ]
Oh, Kyungsoo [2 ]
机构
[1] Chung Ang Univ, Dept Global Innovat Drugs, Seoul 06974, South Korea
[2] Chung Ang Univ, Ctr Metareceptome Res, Grad Sch Pharmaceut Sci, Seoul 06974, South Korea
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期
基金
新加坡国家研究基金会;
关键词
PHOTOREDOX CATALYSIS; CHAIN EXTENSION; KETONES; ANNULATION; CHEMISTRY; YLIDES;
D O I
10.1021/acs.joc.4c02374
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible-light-induced three-component alkoxyalkylation of alkenes has been developed under the photocatalysis of fac-Ir(ppy)3. The alkene substrate scope included aryl and aliphatic alkenes as well as electron-rich and electron-deficient alkenes, allowing the facile coupling with a diverse array of alpha-halocarbonyl compounds. The redox potential-guided orchestration of radical processes with precision allows rapid access to highly functionalized products that are useful building blocks in organic synthesis.
引用
收藏
页码:17621 / 17634
页数:14
相关论文
共 50 条
  • [31] Visible-Light-Driven Three-Component Reaction of Unactivated Alkenes Enables Access to Monofluoro ?-Amino Acids
    Ju, Guodong
    Huang, Zhibin
    Liu, Jian
    Xu, Xu
    Deng, Zefeng
    Zhao, Yingsheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023,
  • [32] Visible-Light Induced Three-Component Dearomatization of Phenols with Oxime Ester and DABSO
    Wei, Hu
    Liu, Hongyuan
    Zhang, Zhen-Dong
    Li, Zhi-Kai
    He, Yong-Ke
    Li, Shaoyu
    Yu, Weijie
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [33] Three-component reactions of halogenotrinitromethanes with alkenes
    Budynina, EM
    Ivanova, OA
    Averina, EB
    Grishin, YK
    Kuznetsova, TS
    Zefirov, NS
    SYNTHESIS-STUTTGART, 2005, (02): : 286 - 290
  • [34] Visible light-induced hydroxymethylation and formylation of (iso) quinolines with alcohols
    Zhang, Yilan
    Yue, Xiaoguang
    Zhu, Jiashun
    Peng, Jiehai
    Zhou, Chenxin
    Wu, Jirong
    Zhang, Pengfei
    MOLECULAR CATALYSIS, 2022, 530
  • [35] Visible light-induced direct α C–H functionalization of alcohols
    Linbin Niu
    Jiamei Liu
    Xing-An Liang
    Shengchun Wang
    Aiwen Lei
    Nature Communications, 10
  • [36] Visible Light-Induced Organophotoredox-Catalyzed β-Hydroxytrifluoromethylation of Unactivated Alkenes
    Behera, Mousumi
    Dharpure, Pankaj D.
    Sahu, Ajit K.
    Bhat, Ramakrishna G.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20): : 14695 - 14709
  • [37] Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes
    Gupta, Subham
    Kundu, Abhishek
    Ghosh, Sumit
    Chakraborty, Amrita
    Hajra, Alakananda
    GREEN CHEMISTRY, 2023, 25 (21) : 8459 - 8493
  • [38] Visible light-induced chemoselective 1,2-diheteroarylation of alkenes
    Guo, Shi-Yu
    Liu, Yi-Peng
    Huang, Jin-Song
    He, Li-Bowen
    He, Gu-Cheng
    Ji, Ding-Wei
    Wan, Boshun
    Chen, Qing-An
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [39] General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis
    Guo, Lei
    Yuan, Mingbin
    Zhang, Yanyan
    Wang, Fang
    Zhu, Shengqing
    Gutierrez, Osvaldo
    Chu, Lingling
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (48) : 20390 - 20399
  • [40] General Method for Selective Three-Component Carboacylation of Alkenes via Visible-Light Dual Photoredox/Nickel Catalysis
    Wang, Zi-Kai
    Wang, Ya-Ping
    Rao, Zhi-Wu
    Liu, Chun-Yu
    Pan, Xian-Hua
    Guo, Lei
    ORGANIC LETTERS, 2023, 25 (10) : 1673 - 1677