Manganese-Catalyzed ortho-C-H Alkenylation of Aromatic N-H Imidates with Alkynes: Versatile Access to Mono-Alkenylated Aromatic Nitriles

被引：90
|
作者：
Yang, Xiaoxu [1 ]
Jin, Xiqing [1 ]
Wang, Congyang [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 15期
基金：
中国国家自然科学基金;
关键词：
alkynes; C-H activation; homogeneous catalysis; manganese; nitriles; 2+2+2 CYCLOADDITION; BOND FUNCTIONALIZATIONS; ACTIVATION; CONSTRUCTION; ALDEHYDES; ROUTE; ACID; CYCLOTRIMERIZATION; ALPHA; OMEGA-DIYNES; ARYLNITRILES;
D O I：
10.1002/adsc.201600128
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
So far, the direct C-H alkenylation of aromatic nitriles with alkynes has not been achieved. Herein, we discribe the first manganese-catalyzed C-H alkenylation of aromatic N-H imidates to access mono-alkenylated aromatic nitriles. The reaction is accelerated by the presence of a catalytic amount of sodium pivalate. This protocol is also highlighted by the simple catalytic system, good compatibility of functional groups, and excellent mono-/dialkenylation selectivity as well as E/Z stereoselectivity.
引用
收藏
页码：2436 / 2442
页数：7
相关论文
共 50 条
  • [1] Manganese-Catalyzed ortho-Alkenylation of Aromatic Amidines with Alkynes via C-H Activation
    Jia, Teng
    Wang, Congyang
    [J]. CHEMCATCHEM, 2019, 11 (21) : 5292 - 5295
  • [2] Manganese-Catalyzed ortho-C-H Amidation of Weakly Coordinating Aromatic Ketones
    Kong, Xianqiang
    Xu, Bo
    [J]. ORGANIC LETTERS, 2018, 20 (15) : 4495 - 4498
  • [3] Manganese-Catalyzed Aromatic C-H Allylation of Ketones
    Ali, Shaukat
    Huo, Jiaqi
    Wang, Congyang
    [J]. ORGANIC LETTERS, 2019, 21 (17) : 6961 - 6965
  • [4] Mn-Catalyzed Aromatic C-H Alkenylation with Terminal Alkynes
    Zhou, Bingwei
    Chen, Hui
    Wang, Congyang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) : 1264 - 1267
  • [5] Manganese-Catalyzed Oxime-Directed ortho-C-H Amidation in Ionic Liquids
    Kong, Xianqiang
    Xu, Bo
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (10) : 1862 - 1865
  • [6] Ruthenium-catalyzed ortho alkenylation of aromatic nitriles with activated alkenes via C-H bond activation
    Reddy, Mallu Chenna
    Jeganmohan, Masilamani
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (53) : 10738 - 10741
  • [7] Rhodium-Catalyzed Alkenylation of C-H Bonds in Aromatic Amides with Alkynes
    Shibata, Kaname
    Natsui, Satoko
    Chatani, Naoto
    [J]. ORGANIC LETTERS, 2017, 19 (09) : 2234 - 2237
  • [8] Rh(I)-Catalyzed Alkylation of ortho-C-H Bonds in Aromatic Amides with Maleimides
    He, Qiyuan
    Yamaguchi, Takuma
    Chatani, Naoto
    [J]. ORGANIC LETTERS, 2017, 19 (17) : 4544 - 4547
  • [9] RuCl3-Catalyzed Alkenylation of Aromatic C-H Bonds with Terminal Alkynes
    Cheng, Kai
    Yao, Bangben
    Zhao, Jinlong
    Zhang, Yuhong
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5309 - 5312
  • [10] Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system
    Obata, Atsushi
    Ano, Yusuke
    Chatani, Naoto
    [J]. CHEMICAL SCIENCE, 2017, 8 (09) : 6650 - 6655
12345