Silver-Catalyzed Carbon Dioxide Fixation on Alkynylindoles

被引:8
|
作者
Uema, Seiya [1 ]
Saito, Kodai [1 ]
Yamada, Tohru [1 ]
机构
[1] Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan
关键词
CARBOXYLATION; INDOLE; CO2;
D O I
10.1021/acs.orglett.2c01994
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
into 2-alkynylindole derivatives was developed to afford tricyclic indoles. Carbon dioxide was selectively fixed on the N atom of the indole, and only 6-endo-dig cyclization proceeded under mild reaction conditions. Carboxylation on C3 of the indole was not observed. This method was applicable for a variety of 2alkynylindoles, and the corresponding products were obtained in high yields without the production of side products.
引用
收藏
页码:4831 / 4834
页数:4
相关论文
共 50 条
  • [1] Silver-catalyzed Reductive Formylation of Amines with Carbon Dioxide
    Uema, Seiya
    Sekine, Kenshiro
    Aoshima, Ryotaro
    Saito, Kodai
    Yamada, Tohru
    CHEMISTRY LETTERS, 2023, 52 (07) : 546 - 548
  • [2] Silver-Catalyzed Carbon Dioxide Incorporation and Rearrangement on Propargylic Derivatives
    Kikuchi, Satoshi
    Yoshida, Shunsuke
    Sugawara, Yuudai
    Yamada, Wataru
    Cheng, Hau-Man
    Fukui, Kosuke
    Sekine, Kohei
    Iwakura, Izumi
    Ikeno, Taketo
    Yamada, Tohru
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2011, 84 (07) : 698 - 717
  • [3] Silver-catalyzed carboxylative cyclization of alkynic hydrazones with carbon dioxide
    Zhang, Wenzhen
    Sun, Yuclian
    Zhang, Min
    Zhou, Hui
    Lu, Xiaobing
    CHINESE JOURNAL OF CATALYSIS, 2019, 40 (08) : 1153 - 1159
  • [4] Silver-Catalyzed Enantioselective Carbon Dioxide Incorporation into Bispropargylic Alcohols
    Yoshida, Shunsuke
    Fukui, Kosuke
    Kikuchi, Satoshi
    Yamada, Tohru
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) : 4072 - +
  • [5] Silver-catalyzed Preparation of Oxazolidinones from Carbon Dioxide and Propargylic Amines
    Yoshida, Shunsuke
    Fukui, Kosuke
    Kikuchi, Satoshi
    Yamada, Tohru
    CHEMISTRY LETTERS, 2009, 38 (08) : 786 - 787
  • [6] Silver-Catalyzed Carboxylation Reaction Using Carbon Dioxide as Carboxylative Reagent
    Zhang, Wen-Zhen
    CARBON DIOXIDE AND ORGANOMETALLICS, 2016, 53 : 73 - 99
  • [7] Silver-Catalyzed Three-Component Coupling of Carbon Dioxide, Amines and α-Diazoesters
    Qi, Chaorong
    Yan, Donghao
    Xiong, Wenfang
    Jiang, Huanfeng
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (05) : 399 - 405
  • [8] Silver-catalyzed carboxylation
    Sekine, K.
    Yamada, T.
    CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) : 4524 - 4532
  • [9] Silver-catalyzed Three-component Reaction of Propargylic Amines, Carbon Dioxide, and N-Bromosuccinimide for Stereoselective Preparation of (E)-Bromovinyloxazolidinones
    Sugiyama, Nao
    Ohseki, Masatoshi
    Kobayashi, Ryo
    Sekine, Kohei
    Saito, Kodai
    Yamada, Tohru
    CHEMISTRY LETTERS, 2017, 46 (09) : 1323 - 1326
  • [10] Silanediol-Catalyzed Carbon Dioxide Fixation
    Hardman-Baldwin, Andrea M.
    Mattson, Anita E.
    CHEMSUSCHEM, 2014, 7 (12) : 3275 - 3278