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
  • [21] Copper(II) Triflate-Catalyzed Three-Component Coupling of Aldehydes, Alkynes and Carbamates
    Dou, Xiao-Yong
    Qi Shuai
    He, Liang-Nian
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2437 - 2440
  • [22] Copper-Catalyzed Synthesis of 1,1-Diborylalkanes through Regioselective Dihydroboration of Terminal Alkynes
    Lee, Sumin
    Li, Dingxi
    Yun, Jaesook
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) : 2440 - 2443
  • [23] Iron-Catalyzed Ligand-Free Three-Component Coupling Reactions of Aldehydes, Terminal Alkynes, and Amines
    Li, Pinhua
    Zhang, Yicheng
    Wang, Lei
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) : 2045 - 2049
  • [24] Copper-Catalyzed Three-Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines
    Yu, Dingyi
    Zhang, Yugen
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (01) : 163 - 169
  • [25] Efficient Synthesis of N-Sulfonylacetamidines from Propiolic Acid by Copper-Catalyzed Three-Component Coupling Reactions
    Xu, Mei
    Kuang, Chunxiang
    Wang, Zhuo
    Yang, Qing
    SYNLETT, 2010, (17) : 2664 - 2666
  • [26] Nickel-catalyzed three-component coupling reaction of terminal alkynes, dihalomethane and amines to propargylamines
    Lanke, Satish R.
    Bhanage, Bhalchandra M.
    APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (12) : 729 - 733
  • [27] Synthesis of Trisubstituted Alkenylstannanes through Copper-Catalyzed Three-Component Coupling of Alkylboranes, Alkynoates, and Tributyltin Methoxide
    Wakamatsu, Takamichi
    Nagao, Kazunori
    Ohmiya, Hirohisa
    Sawamura, Masaya
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) : 11620 - 11623
  • [28] Synthesis of Propiolic Acids via Copper-Catalyzed Insertion of Carbon Dioxide into the C-H Bond of Terminal Alkynes
    Goossen, Lukas J.
    Rodriguez, Nuria
    Manjolinho, Filipe
    Lange, Paul P.
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 2913 - 2917
  • [29] Catalytic Domino Three-Component Synthesis of Functionalized Heterocycles from Carbon Dioxide
    Shi, Wangyu
    Qiao, Chang
    Benet-Buchholz, Jordi
    Kleij, Arjan W.
    CHEMSUSCHEM, 2024, 17 (06)
  • [30] Consecutive Three-Component Synthesis of 2,6-Disubstituted Pyrimid-4(3H)-ones and 1,5-Disubstituted 3-Hydroxypyrazoles Initiated by Copper(I)-Catalyzed Carboxylation of Terminal Alkynes
    Schreiner, Ella
    Braun, Stephan
    Kwasnitschka, Christiane
    Frank, Walter
    Mueller, Thomas J. J.
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 3135 - 3147
12345