Palladium-Catalyzed Heck-Type Coupling via C-N Cleavage

被引:3
|
作者
Fan, Weizheng [1 ]
Liu, Faming [1 ]
Feng, Bainian [1 ]
机构
[1] Jiangnan Univ, Sch Pharmaceut Sci, Wuxi 214122, Peoples R China
基金
中国国家自然科学基金;
关键词
palladium-catalyzed; Heck-type coupling; C-N cleavage; control experiment; mechanism; CARBONYL-COMPOUNDS; DIRECT ARYLATION; MANNICH-BASES; BOND; CHALCONES; FUNCTIONALIZATION; (HETERO)ARENES; OLEFINATION; SEQUENCE; KETONES;
D O I
10.1055/s-0034-1379911
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed Heck-type coupling method between arenes and ketone Mannich bases via C-N cleavage to synthesize chalcones is reported. This protocol offers good yields and tolerates a broad range of functional groups. Based on the extensive experimental data, we propose a plausible coulping mechanism.
引用
收藏
页码:1253 / 1257
页数:5
相关论文
共 50 条
  • [1] Suzuki Coupling of Amides via Palladium-Catalyzed C-N Cleavage of N-Acylsaccharins
    Wu, Hongxiang
    Li, Yue
    Cui, Ming
    Jian, Junsheng
    Zeng, Zhuo
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) : 3876 - 3880
  • [2] Palladium-Catalyzed Suzuki Cross-Coupling of Arylhydrazines via C-N Bond Cleavage
    Peng, Zhimin
    Hu, Gaobo
    Qiao, Hongwei
    Xu, Pengxiang
    Gao, Yuxing
    Zhao, Yufen
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (06) : 2733 - 2738
  • [3] Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
    Teng, Shenghan
    Tessensohn, Malcolm E.
    Webster, Richard D.
    Zhou, Jianrong Steve
    ACS CATALYSIS, 2018, 8 (08): : 7439 - 7444
  • [4] Palladium-Catalyzed Desulfitative Heck-Type Reaction of Aryl Sulfinic Acids with Alkenes
    Wang, Guan-Wu
    Miao, Tao
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) : 5787 - 5790
  • [5] Palladium-Catalyzed Domino Dehydrogenation/Heck-Type Reactions of Carbonyl Compounds
    Le Bras, Jean
    Muzart, Jacques
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2411 - 2428
  • [6] Palladium-Catalyzed Suzuki Coupling ofN-Acyloxazolidinones via Selective Cleavage of C-N Bonds
    Jian, Junsheng
    He, Zhanyu
    Zhang, Yuqi
    Liu, Tingting
    Liu, Lizhen
    Wang, Zijia
    Wang, Hui
    Wang, Sanyong
    Zeng, Zhuo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4176 - 4180
  • [7] Palladium-catalyzed coupling of azoles with 1-aryltriazenes via C-H/C-N cleavage
    Dai, Wei-Can
    Wang, Zhong-Xia
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1281 - 1288
  • [8] Palladium-Catalyzed Decarboxylative Heck-Type Coupling of Activated Aliphatic Carboxylic Acids Enabled by Visible Light
    Koy, Maximilian
    Sandfort, Frederik
    Tlahuext-Aca, Adrian
    Quach, Linda
    Daniliuc, Constantin G.
    Glorius, Frank
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (18) : 4552 - 4555
  • [9] Palladium-Catalyzed Oxidative Heck-Type Allylation of β,β-Disubstituted Enones with Allyl Carbonates
    Jin, Weiwei
    Yang, Qin
    Wu, Ping
    Chen, Jiping
    Yu, Zhengkun
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 2097 - 2102
  • [10] Palladium-catalyzed cascade Heck-type thiocarbonylation for the synthesis of functionalized thioesters
    Xu, Ren-Rui
    Wang, Wei
    Qi, Xinxin
    Wu, Xiao-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (05) : 1417 - 1421