Iridium-catalyzed addition of acid chlorides to terminal alkynes

被引：0
|
作者：
Iwai, Tomohiro [1 ]
Fujihara, Tetsuaki [1 ]
Terao, Jun [1 ]
Tsuji, Yasushi [1 ]
机构：
[1] Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan
来源：
Journal of the American Chemical Society | 2009年 / 131卷 / 19期
关键词：
(Chemical Equation Presented) An iridium N-heterocyclic carbene (NHC) complex, IrCl(cod)(IPr), successfully catalyzed an addition of common aromatic acid chlorides to terminal alkynes to afford (Z)-β-chloro-α,β- unsaturated ketones regio- and stereoselectively. When the NHC ligand (IPr) was changed to a phosphine (RuPhos), the addition occurred with decarbonylation to give the corresponding (Z)-vinyl chlorides. Furthermore, the former reaction using IrCl(cod)(IPr) can be applied to the catalytic synthesis of 2,5-disubstituted furans. Copyright © 2009 American Chemical Society;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Journal article (JA)
引用
收藏
页码：6668 / 6669
相关论文
共 50 条
  • [31] Iridium-Catalyzed Hydrogenation of Carboxylic Acid Esters
    Junge, Kathrin
    Wendt, Bianca
    Jiao, Haijun
    Beller, Matthias
    CHEMCATCHEM, 2014, 6 (10) : 2810 - 2814
  • [32] Electrooxidative Iridium-Catalyzed Regioselective Annulation of Benzoic Acids with Internal Alkynes
    Yang, Qi-Liang
    Jia, Hong-Wei
    Liu, Ying
    Xing, Yi-Kang
    Ma, Rui-Cong
    Wang, Man-Man
    Qu, Gui-Rong
    Mei, Tian-Sheng
    Guo, Hai-Ming
    ORGANIC LETTERS, 2021, 23 (04) : 1209 - 1215
  • [33] Rhodium- or iridium-catalyzed trans-hydroboration of terminal alkynes, giving (Z)-1-alkenylboron compounds
    Ohmura, T
    Yamamoto, Y
    Miyaura, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) : 4990 - 4991
  • [34] Stereodefined Skipped Dienes through Iridium-Catalyzed Formal Addition of Tertiary Allylic C-H Bonds to Alkynes
    Wang, Zi-Xuan
    Gao, Peng-Chao
    Lin, En-Ze
    Li, Bi-Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (26)
  • [35] Iridium-Catalyzed Silylation
    Iglesias, Manuel
    Oro, Luis A.
    IRIDIUM CATALYSTS FOR ORGANIC REACTIONS, 2021, 69 : 227 - 270
  • [36] Iridium-catalyzed regioselective hydrosilylation of internal alkynes facilitated by directing and steric effects
    Gao, Weiwei
    Ding, Huan
    Yu, Tian
    Wang, Zhen
    Ding, Shengtao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (28) : 6216 - 6220
  • [37] Iridium-Catalyzed Aerobic Coupling of Salicylaldehydes with Alkynes: A Remarkable Switch of Oxacyclic Product
    Yamane, Shintaro
    Hinoue, Tomoaki
    Usuki, Yoshinosuke
    Itazaki, Masumi
    Nakazawa, Hiroshi
    Hayashi, Yoshihiro
    Kawauchi, Susumu
    Miura, Masahiro
    Satoh, Tetsuya
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (31) : 7852 - 7855
  • [38] Rhodium- and iridium-catalyzed oxidative coupling of benzoic acids with alkynes and alkenes
    Satoh, Tetsuya
    Ueura, Kenji
    Miura, Masahiro
    PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 1127 - 1134
  • [39] Iridium(I)-Catalyzed Atroposelective Alkenylation of Heterobiaryls with Terminal Alkynes
    Xiong, Maoqian
    Chen, Feifei
    Shu, Yuhang
    Wu, Xiang
    Tang, Jie
    Yang, Fan
    Xing, Dong
    ORGANIC LETTERS, 2023, 25 (31) : 5703 - 5708
  • [40] Alkoxide-catalyzed addition of terminal alkynes to ketones
    Babler, JH
    Liptak, VP
    Phan, N
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01): : 416 - 417
12345