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
  • [21] Palladium-Catalyzed C-N Coupling of Pyrazole Amides with Triazolo- and Imidazopyridine Bromides in Ethanol
    Bliss, Fritz
    Fantasia, Serena
    Le Coz, Erwann
    Puntener, Kurt
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2021, 25 (03) : 457 - 468
  • [22] Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones
    Li, Jun
    Chi, Xiaochen
    Meng, Long
    Jiao, Luyang
    Shang, Wenhui
    Wang, Ping
    Zhang, Daopeng
    Dong, Yunhui
    Liu, Qing
    Liu, Hui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (40) : 7356 - 7360
  • [23] Phosphaannulation of Aryl- and Benzylphosphonic Acids with Unactivated Alkenes via Palladium-Catalyzed C-H Activation/Oxidative Cyclization Reaction
    Jeon, Woo Hyung
    Son, Jeong-Yu
    Kim, Sun-Eung
    Lee, Phil Ho
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (04) : 811 - 817
  • [24] Palladium-catalyzed Suzuki-Miyaura coupling with aryl and heteroaryl bromides using N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine
    Wang, Kun
    Yi, Tao
    Yu, Xiaojun
    Zheng, Xueli
    Fu, Haiyan
    Chen, Hua
    Li, Ruixiang
    APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (07) : 342 - 346
  • [25] Palladium-Catalyzed Direct Arylation of Imidazolone N-Oxides with Aryl Bromides and Its Application in the Synthesis of GSK2137305
    Zhao, He
    Wang, Ruifang
    Chen, Ping
    Gregg, Brian T.
    Hsia, Ming Min
    Zhang, Wei
    ORGANIC LETTERS, 2012, 14 (07) : 1872 - 1875
  • [26] A palladium-catalyzed dehydrative N-benzylation/C-H benzylation cascade of 2-morpholinoanilines on water
    Hikawa, Hidemasa
    Ichinose, Risa
    Kikkawa, Shoko
    Azumaya, Isao
    GREEN CHEMISTRY, 2018, 20 (06) : 1297 - 1305
  • [27] Design and Synthesis of Planar-Chiral Oxazole-Pyridine N,N-Ligands: Application in Palladium-Catalyzed Asymmetric Acetoxylative Cyclization
    Bai, Yu-Qing
    Wang, Xin-Wei
    Wu, Bo
    Wang, Xiao-Qing
    Liao, Rong-Zheng
    Li, Man
    Zhou, Yong-Gui
    ACS CATALYSIS, 2023, 13 (14) : 9829 - 9838
  • [28] Metal-Catalyzed Sequential Formation of Distant Bonds in Organic Molecules: Palladium-Catalyzed Hydrosilylation/Cyclization of 1,n-Dienes by Chain Walking
    Kochi, Takuya
    Ichinose, Kazuya
    Shigekane, Masayuki
    Hamasaki, Taro
    Kakiuchi, Fumitoshi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (16) : 5261 - 5265
  • [29] Palladium-catalyzed cross-coupling of cyclopropylmethyl N-tosylhydrazones with aromatic bromides: an easy access to multisubstituted 1,3-butadienes
    Yang, Qin
    Chai, Huining
    Liu, Tingting
    Yu, Zhengkun
    TETRAHEDRON LETTERS, 2013, 54 (48) : 6485 - 6489
  • [30] Modular Synthesis of Quinazolinone-Fused Phenanthridinones by a Palladium-Catalyzed Cascade C-H/N-H Arylation Process
    Yu, Yanhan
    Yue, Yixia
    Wang, Deqiang
    Li, Xue
    Chen, Chunxia
    Peng, Jinsong
    SYNTHESIS-STUTTGART, 2016, 48 (22): : 3941 - 3950