Photoinduced Palladium-Catalyzed Intermolecular Radical Cascade Cyclization of N-Arylacrylamides with Unactivated Alkyl Bromides

被引:42
|
作者
Du, Juan [1 ,2 ]
Wang, Xing [1 ]
Wang, Hongling [1 ]
Wei, Jinhu [1 ]
Huang, Xuan [1 ]
Song, Jun [2 ]
Zhang, Junmin [1 ]
机构
[1] Shenzhen Univ, Coll Chem & Environm Engn, Int Joint Res Ctr Mol Sci, Shenzhen 518060, Peoples R China
[2] Shenzhen Univ, Coll Phys & Optoelect Engn, Shenzhen 518060, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND FORMATION; COMPLEXES; OXIDATION;
D O I
10.1021/acs.orglett.1c01698
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild visible-light-induced Pd-catalyzed intermolecular radical cascade reaction of N- arylacrylamides with unactivated alkyl bromides is disclosed. Photoexcited Pd complexes transfer a single electron in this protocol, and hybrid alkyl Pd-radical species are involved as the key reaction intermediates. Sophisticated bioactive oxindole derivatives bearing various substituents and substitution patterns can be efficiently afforded through this approach.
引用
收藏
页码:5631 / 5635
页数:5
相关论文
共 35 条
  • [1] Palladium-Catalyzed Alkoxycarbonylation of Unactivated Secondary Alkyl Bromides at Low Pressure
    Sargent, Brendon T.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (24) : 7520 - 7523
  • [2] Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis
    Venning, Alexander R. O.
    Kwiatkowski, Megan R.
    Pena, Joan E. Roque
    Lainhart, Brendan C.
    Guruparan, Akil A.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (33) : 11595 - 11600
  • [3] An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes
    Iglesias, Alvaro
    Perez, Edwin G.
    Muniz, Kilian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) : 8109 - 8111
  • [4] Palladium-Catalyzed Asymmetric Intermolecular Cyclization
    Hu, Jian
    Hirao, Hajime
    Li, Yongxin
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) : 8676 - 8680
  • [5] Visible-Light-Driven Palladium-Catalyzed Radical Alkylation of C-H Bonds with Unactivated Alkyl Bromides
    Zhou, Wen-Jun
    Cao, Guang-Mei
    Shen, Guo
    Zhu, Xing-Yong
    Gui, Yong-Yuan
    Ye, Jian-Heng
    Sun, Liang
    Liao, Li-Li
    Li, Jing
    Yu, Da-Gang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) : 15683 - 15687
  • [6] Free Radical Cyclization of N-Arylacrylamides: Mild and Facile Synthesis of 3-Thiocyanato Oxindoles
    Karmaker, Pran Gopal
    Qiu, Jiashen
    Wu, Di
    Yin, Hongquan
    Chen, Fu-Xue
    SYNLETT, 2018, 29 (07) : 954 - +
  • [7] Palladium-Catalyzed Highly Diastereoselective Oxidative Cascade Cyclization Reactions
    Yip, Kai-Tai
    Zhu, Nian-Yong
    Yang, Dan
    ORGANIC LETTERS, 2009, 11 (09) : 1911 - 1914
  • [8] Palladium-catalyzed difunctionalization/dearomatization of N-benzylacrylamides with α-carbonyl alkyl bromides: facile access to azaspirocyclohexadienones
    Peng, Chuan-Chong
    Wu, Li-Jun
    Pi, Shao-Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (35) : 7602 - 7606
  • [9] Palladium-Catalyzed Cross Coupling of Secondary and Tertiary Alkyl Bromides with a Nitrogen Nucleophile
    Peacock, D. Matthew
    Roos, Casey B.
    Hartwig, John F.
    ACS CENTRAL SCIENCE, 2016, 2 (09) : 647 - 652
  • [10] Palladium-Catalyzed Heck-Type Cross-Couplings of Unactivated Alkyl Iodides
    McMahon, Caitlin M.
    Alexanian, Erik J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) : 5974 - 5977