Cu(I)-Catalyzed Carboxylative Coupling of Terminal Alkynes, Allylic Chlorides, and CO2

被引:134
|
作者
Zhang, Wen-Zhen [1 ]
Li, Wen-Jie [1 ]
Zhang, Xiao [1 ]
Zhou, Hui [1 ]
Lu, Xiao-Bing [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China
基金
中国国家自然科学基金;
关键词
N-HETEROCYCLIC CARBENES; CARBON-DIOXIDE; CATALYZED CARBOXYLATION; STEREOSELECTIVE-SYNTHESIS; ALKENYLBORONIC ESTERS; COPPER(I); 2-ALKYNOATES; CYCLIZATION; COMPLEXES; CHEMISTRY;
D O I
10.1021/ol102172v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly selective synthesis of a variety of functionalized allylic 2-alkynoates was realized via the carboxylative coupling of terminal alkynes, allylic chlorides, and CO2 catalyzed by the N-heterocyclic carbene copper(I) complex (IPr)CuCl. The catalyst can be easily recovered without any loss in activity and product selectivity.
引用
收藏
页码:4748 / 4751
页数:4
相关论文
共 50 条
  • [21] 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
  • [22] Metal Catalyzed Carboxylative Coupling of Terminal Alkynes, Organohalides and Carbon Dioxide: A Novel and Promising Synthetic Strategy toward 2-Alkynoates (A Review)
    Vessally, Esmail
    Hosseinian, Akram
    Babazadeh, Mirzaagha
    Edjlali, Ladan
    Hosseinzadeh-Khanmiri, Rahim
    CURRENT ORGANIC CHEMISTRY, 2018, 22 (04) : 315 - 322
  • [23] Cu(I)-catalyzed aerobic cross-dehydrogenative coupling of terminal alkynes with thiols for the construction of alkynyl sulfides
    Yang, Yong
    Dong, Weibing
    Guo, Yisong
    Rioux, Robert M.
    GREEN CHEMISTRY, 2013, 15 (11) : 3170 - 3175
  • [24] Cu(I)-catalyzed coupling of diaryldiazomethanes with terminal alkynes: an efficient synthesis of tri-aryl-substituted allenes
    Wu, Chenggui
    Hu, Fangdong
    Liu, Zhenxing
    Deng, Guisheng
    Ye, Fei
    Zhang, Yan
    Wang, Jianbo
    TETRAHEDRON, 2015, 71 (49) : 9196 - 9201
  • [25] C?H Carboxylation of Terminal Alkynes Catalyzed by Low Loadings of Silver(I)/DMSO at Ambient CO2 Pressure
    Arndt, Matthias
    Risto, Eugen
    Krause, Thilo
    Goossen, Lukas J.
    CHEMCATCHEM, 2012, 4 (04) : 484 - 487
  • [26] Silica-catalyzed carboxylative cyclization of propargylic amines with CO2
    Matsuo, Hideaki
    Choi, Jun-Chul
    Fujitani, Tadahiro
    Fujita, Ken-ichi
    TETRAHEDRON LETTERS, 2020, 61 (48)
  • [27] Electrochemically Mediated Carboxylative Cyclization of Allylic/ Homoallylic Amines with CO2 at Ambient Pressure
    Pan, Yong-Zhou
    Xia, Qiang
    Zhu, Jin-Xiu
    Wang, Ying-Chun
    Liang, Ying
    Wang, Hengshan
    Tang, Hai-Tao
    Pan, Ying-Ming
    ORGANIC LETTERS, 2022, : 8239 - 8243
  • [28] 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
  • [29] 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):
  • [30] Iridium-catalyzed addition of acid chlorides to terminal alkynes
    Iwai, Tomohiro
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    Journal of the American Chemical Society, 2009, 131 (19): : 6668 - 6669