Synthesis of Isocoumarins through Three-Component Couplings of Arynes, Terminal Alkynes, and Carbon Dioxide Catalyzed by an NHC-Copper Complex

被引：95
|
作者：
Yoo, Woo-Jin [1 ]
Nguyen, Thanh V. Q. [1 ]
Kobayashi, Shu [1 ]
机构：
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 38期
基金：
日本科学技术振兴机构; 日本学术振兴会;
关键词：
alkynes; arynes; carbon dioxide; copper; multicomponent reactions; 3-SUBSTITUTED ISOCOUMARINS; INTRAMOLECULAR CYCLIZATION; ACID-DERIVATIVES; CARBOXYLIC-ACIDS; BENZOIC-ACIDS; H BONDS; CO2; TRANSFORMATION; ESTERS; PHTHALIDES;
D O I：
10.1002/anie.201404692
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A copper-catalyzed multicomponent coupling reaction between in situ generated ortho-arynes, terminal alkynes, and carbon dioxide was developed to access isocoumarins in moderate to good yields. The key to this CO2-incorporating reaction was the use of a versatile N-heterocyclic carbene/copper complex that was able to catalyze multiple transformations within the three-component reaction.
引用
收藏
页码：10213 / 10217
页数：5
相关论文
共 50 条
  • [1] Copper-Catalyzed Three-Component Borylstannylation of Alkynes
    Takemoto, Yuki
    Yoshida, Hiroto
    Takaki, Ken
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (46) : 14841 - 14844
  • [2] Photoinduced Copper-Catalyzed Regioselective Synthesis of Indoles: Three-Component Coupling of Arylamines, Terminal Alkynes, and Quinones
    Sagadevan, Arunachalam
    Ragupathi, Ayyakkannu
    Hwang, Kuo Chu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 13896 - 13901
  • [3] Three-Component Coupling of Aldehydes, Amines, and Alkynes Catalyzed by Oxidized Copper Nanoparticles on Titania
    Jose Albaladejo, Maria
    Alonso, Francisco
    Moglie, Yanina
    Yus, Miguel
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (16) : 3093 - 3104
  • [4] Palladium-catalyzed, sequential, three-component cross-coupling of aryl halides, alkynes, and arynes
    Liu, Zhijian
    Larock, Richard C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) : 2535 - 2538
  • [5] A Cooperative Copper- and Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Epoxides, and Terminal Alkynes
    Jeganmohan, Masilanzani
    Bhuvaneswari, Sivakolundu
    Cheng, Chien-Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (02) : 391 - 394
  • [6] Silver iodide catalyzed the three-component reaction between terminal alkynes, carbon disulfide, and aziridines
    Samzadeh-Kermani, A.
    JOURNAL OF SULFUR CHEMISTRY, 2019, 40 (05) : 554 - 564
  • [7] Stereoselective Synthesis of Functionalized 1,3-Enynes through Recyclable Copper(I)-Catalyzed Three-Component Reaction of Terminal Alkynes, Diazoesters and Aldehydes
    Ye, Qian
    Liao, Yang
    Luo, Chengkai
    Cai, Mingzhong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (05)
  • [8] Highly Regio- and Stereoselective Three-Component Nickel-Catalyzed syn-Hydrocarboxylation of Alkynes with Diethyl Zinc and Carbon Dioxide
    Li, Suhua
    Yuan, Weiming
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) : 2578 - 2582
  • [9] Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide
    Mei, Congmin
    Zhao, Yibo
    Chen, Qianwei
    Cao, Changsheng
    Pang, Guangsheng
    Shi, Yanhui
    CHEMCATCHEM, 2018, 10 (14) : 3057 - 3068
  • [10] Synthesis of N-Arylated 1,2-Dihydroheteroaromatics Through the Three-Component Reaction of Arynes with N-Heteroaromatics and Terminal Alkynes or Ketones
    Jeganmohan, Masilamani
    Bhuvaneswari, Sivakolundu
    Cheng, Chien-Hong
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (01) : 153 - 159
12345