Palladium-catalyzed cascade metallo-ene/Suzuki coupling reaction of allenamides

被引:34
|
作者
Liang, Hanbing [1 ]
Yan, Fachao [1 ]
Dong, Xu [1 ]
Liu, Qing [1 ]
Wei, Xiaobing [1 ]
Liu, Sheng [2 ]
Dong, Yunhui [1 ]
Liu, Hui [1 ,2 ,3 ]
机构
[1] Shandong Univ Technol, Sch Chem Engn, 266 West Xincun Rd, Zibo 255049, Peoples R China
[2] Zibo Entry & Exit Inspect & Quarantine Bur, Tech Ctr, Zibo 255031, Peoples R China
[3] Hunan Univ, Coll Mat Sci & Engn, Changsha 410082, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
OXIDATIVE CARBOCYCLIZATION-BORYLATION; PEPTIDASE-IV INHIBITOR; C BOND FORMATION; ENE REACTIONS; ARYLATING CARBOCYCLIZATION; CARBONYLATION-ALKYNYLATION; REGIOSELECTIVE SYNTHESIS; CYCLOISOMERIZATION; CYCLIZATION; 1,6-DIENES;
D O I
10.1039/c7cc00191f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new type of cascade metallo-ene/Suzuki coupling reaction of allenamides catalyzed by palladium is described. A variety of polyfunctionalized 2,3-dihydropyrrole derivatives, which are important structural motifs for bioactive molecules, were furnished with excellent yields. Two new Csp(3)-Csp(2) bonds were constructed in one pot efficiently. The reductive elimination from p-allyl palladium complex presented excellent regioselectivity to the terminal C1 position. The unique terminal alkene was one of the most easily functionalized groups, providing these molecules with a potential transformation to much more complicated molecules.
引用
收藏
页码:3138 / 3141
页数:4
相关论文
共 50 条
  • [41] Palladium-catalyzed Suzuki cross-coupling of N′-tosyl arylhydrazines
    Liu, Jin-Biao
    Yan, Hui
    Chen, Hui-Xuan
    Luo, Yu
    Weng, Jiang
    Lu, Gui
    CHEMICAL COMMUNICATIONS, 2013, 49 (46) : 5268 - 5270
  • [42] Palladium-catalyzed Suzuki-Miryaura coupling reactions using neopentylphosphines
    Brown, William S.
    Pair, Emily
    Sonnier, Quientin
    Khan, Maryam
    Shaughnessy, Kevin H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [43] Palladium-Catalyzed Suzuki Cross-Coupling of Phenylhydrazine or (Phenylsulfonyl)hydrazine
    Li, Yahui
    Liu, Wei
    Tian, Qingshan
    Yang, Qing
    Kuang, Chunxiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (16) : 3307 - 3312
  • [44] Tandem palladium-catalyzed borylation and Suzuki coupling (BSC) to thienocarbazole precursors
    Ferreira, ICFR
    Queiroz, MJRP
    Kirsch, G
    TETRAHEDRON LETTERS, 2003, 44 (23) : 4327 - 4329
  • [45] A General Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Mesylates
    So, Chau Ming
    Lau, Chak Po
    Kwong, Fuk Yee
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8059 - 8063
  • [46] Efficient and diastereoselective synthesis of (+)-goniobutenolide A via palladium-catalyzed ene-yne cross coupling lactonization cascade
    Kotora, M
    Negishi, E
    TETRAHEDRON LETTERS, 1996, 37 (50) : 9041 - 9042
  • [48] Highly selective Palladium-catalyzed Suzuki coupling reaction toward chlorine-containing electroluminescence polymers
    Zhang, Yubao
    Gao, Xiang
    Li, Junli
    Tu, Guoli
    DYES AND PIGMENTS, 2015, 120 : 112 - 117
  • [49] Advance on Applications of Microwave Technique in Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction
    Li, Qinghan
    Ding, Yong
    Zhang, Gang
    Zhang, Zhen
    Mo, Song
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (01) : 83 - 104
  • [50] Palladium-catalyzed Suzuki-Miyaura coupling reaction of unprotected nitrogen-rich heteroaryl halide
    Tan, Jiajing
    Chen, Yonggang
    Li, Hongmei
    Yasuda, Nobuyoshi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248