A highly effective Pd/Cu-catalyzed coupling reaction of terminal alkynes with organic halides promoted by tetrabutylammonium fluoride or hydroxide

被引：0
|
作者：
Mori, A [1 ]
Shimada, T [1 ]
Kondo, T [1 ]
Sekiguchi, A [1 ]
机构：
[1] Tokyo Inst Technol, Chem Resources Lab, Yokohama, Kanagawa 2268503, Japan
来源：
SYNLETT | 2001年 / 05期
关键词：
Sonogashira-Hagihara coupling; Pd/Cu catalyst; terminal alkynes; tetrabutylammonium fluoride; tetrabutylammonium hydroxide; polycondensation;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Coupling reaction of terminal alkynes catalyzed by Pd/ Cu with several organic electrophiles is shown to proceed by use of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide(TBAOH) as an activator. Treatment of l-octyne and 4-methoxy-iodobenzene in the presence of 2.0 equiv of TBAOH, 1 mol% of PdCl2(PPh3)(3), and 2 mol% of Cul affords: 1-phenyl-1-octyne in 98% yield after stirring at room temperature for 1 h. The new coupling reaction is also applied to polymer synthesis via polycondensation of a diyne and a diiodoarene.
引用
收藏
页码：649 / 651
页数：3
相关论文
共 50 条
  • [1] Tetrabutylammonium Bromide (TBAB)-Promoted, Pd/Cu-Catalyzed Sonogashira Coupling of N-Tosyl Aryltriazenes
    Cao, Jun
    Ding, Wenbin
    Zou, Gang
    ORGANIC LETTERS, 2024, 26 (21) : 4576 - 4580
  • [2] The origin of regioselectivity in Cu-catalyzed hydrocarbonylative coupling of alkynes with alkyl halides
    Liu, Shengnan
    Liu, Jianbiao
    Wang, Qiong
    Wang, Jin
    Huang, Fang
    Wang, Wenjuan
    Sun, Chuanzhi
    Chen, Dezhan
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (09): : 1137 - 1148
  • [3] New activators for the coupling reaction of terminal alkynes with organic halides
    Ahmed, MSM
    Sekiguchi, A
    Shimada, T
    Kawashima, J
    Mori, A
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (02) : 327 - 330
  • [4] Aerobic Cu-catalyzed oxidative 1: 2 coupling of benzynes with terminal alkynes
    Lu, Tianhao
    Shen, Yong
    Wang, Min
    Zhang, Zibing
    Li, Shijun
    Xie, Chunsong
    CHEMICAL COMMUNICATIONS, 2020, 56 (59) : 8214 - 8217
  • [5] Synthesis of Internal Alkynes through the Pd-Catalyzed Coupling of Heteroaryl Halides with Terminal Alkynes
    Lu, Linhua
    Yan, Hong
    Sun, Peng
    Zhu, Yan
    Yang, Hailong
    Liu, Defu
    Rong, Guangwei
    Mao, Jincheng
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (09) : 1644 - 1648
  • [6] Synthesis of Allylic Alcohols via Cu-Catalyzed Hydrocarbonylative Coupling of Alkynes with Alkyl Halides
    Mankad, Neal P. (npm@uic.edu), 1600, American Chemical Society (140):
  • [7] Synthesis of Allylic Alcohols via Cu-Catalyzed Hydrocarbonylative Coupling of Alkynes with Alkyl Halides
    Cheng, Li-Jie
    Islam, Shahidul M.
    Mankad, Neal P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (03) : 1159 - 1164
  • [8] Palladium-catalyzed three-component coupling reaction of organic halides, norbornadiene and terminal alkynes
    Chang, Yu-Cheng
    Kuo, Chun-Jung
    Li, Chen-Shun
    Liu, Charng-Hsing
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (23) : 4982 - 4989
  • [9] Cu/Oxalic Diamide-Catalyzed Coupling of Terminal Alkynes with Aryl Halides
    Chen, Ying
    Li, Sailuo
    Xu, Lanting
    Ma, Dawei
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 3330 - 3334
  • [10] Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate
    Ming, Xiao-Xia
    Wu, Shuai
    Tian, Ze-Yu
    Song, Jia-Wei
    Zhang, Cheng-Pan
    ORGANIC LETTERS, 2021, 23 (17) : 6795 - 6800
12345