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
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
  • [41] Supported nano gold catalyzed three-component coupling reactions of amines, dichloromethane and terminal alkynes (AHA)
    Berrichi, Amina
    Bachir, Redouane
    Benabdallah, Mohamed
    Choukchou-Braham, Noureddine
    TETRAHEDRON LETTERS, 2015, 56 (11) : 1302 - 1306
  • [42] Copper-catalyzed three-component reactions of phenols, acyl chlorides and Wittig reagents for the synthesis of β-aryloxyl acrylates
    Zhang, Yi
    Liu, Yunyun
    Wan, Jie-Ping
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (03) : 1567 - 1569
  • [43] A copper(I)-catalyzed three-component reaction of triethoxysilanes, sulfur dioxide, and alkyl halides
    Zheng, Danqing
    Mao, Runyu
    Li, Zhiming
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (03): : 359 - 363
  • [44] Copper(I)-Catalyzed Three-Component Coupling of N-Tosylhydrazones, Alkynes and Azides: Synthesis of Trisubstituted 1,2,3-Triazoles
    Zhang, Zhikun
    Zhou, Qi
    Ye, Fei
    Xia, Ying
    Wu, Guojiao
    Hossain, Mohammad Lokman
    Zhang, Yan
    Wang, Jianbo
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2277 - 2286
  • [45] A Copper(I)-Catalyzed Three-Component Domino Process: Assembly of Complex 1,2,3-Triazolyl-5-Phosphonates from Azides, Alkynes, and H-Phosphates
    Li, Lingjun
    Hao, Guoliang
    Zhu, Anlian
    Fan, Xincui
    Zhang, Guisheng
    Zhang, Lihe
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (43) : 14403 - 14406
  • [46] Synthesis of Lithium Boracarbonate Ion Pairs by Copper-Catalyzed Multi-Component Coupling of Carbon Dioxide, Diboron, and Aldehydes
    Carry, Beatrice
    Zhang, Liang
    Nishiura, Masayoshi
    Hou, Zhaomin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (21) : 6257 - 6260
  • [47] Copper-Catalyzed Three-Component Synthesis of 2-Iminodihydrocoumarins and 2-Iminocoumarins
    Shen, Yang
    Cui, Sunliang
    Wang, Jing
    Chen, Xiaopeng
    Lu, Ping
    Wang, Yanguang
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) : 1139 - 1144
  • [48] Palladium-catalyzed three-component coupling of propargylic oxiranes, phenols and carbon dioxide
    Yoshida, Masahiro
    Murao, Tomohiko
    Sugimoto, Kenji
    Ihara, Masataka
    SYNLETT, 2007, (04) : 575 - 578
  • [49] Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction
    Gommermann, Nina
    Knochel, Paul
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) : 4380 - 4392
  • [50] Palladium-catalyzed intermolecular three-component coupling of organic halides with Alkynes and alkenes: Efficient synthesis of oligoene compounds
    Shibata, Kana
    Satoh, Tetsuya
    Miura, Masahiro
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (14-15) : 2317 - 2325