Gold-Catalyzed Alkyne Multifunctionalization through an Oxidation-Oxyalkylation-Aryloxylation Sequence

被引:5
|
作者
Xiong, Weichen [1 ]
Zhou, Su [1 ]
Zhang, Xinke [1 ]
Zhao, Jingyu [1 ]
Huang, Jingjing [1 ]
Hu, Wenhao [1 ]
Xu, Xinfang [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
TERMINAL ALKYNES; METHYL KETONES; ACTIVATION; ARYLATION;
D O I
10.1021/acs.orglett.2c04115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A gold-catalyzed oxidative three-component reaction of terminal alkynes with alcohols and quinone monoimines has been disclosed, affording alpha-ketoacetals in good to excellent yields. By using quinone monoimines as electrophiles for the interception of the in situ generated gold enolate intermediate, this one-pot process provides an unprecedented method for the polyfunctionalization of terminal alkynes through an oxidation-oxyalkylation- aryloxylation sequence, installing three oxygen atoms on the C-C triple bond.
引用
收藏
页码:405 / 409
页数:5
相关论文
共 50 条
  • [41] Rapid Access to Chroman-3-ones through Gold-Catalyzed Oxidation of Propargyl Aryl Ethers
    Wang, Yanzhao
    Ji, Kegong
    Lan, Sylvester
    Zhang, Liming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) : 1915 - 1918
  • [42] Straightforward and Highly Efficient Synthesis of -Acetoxy Ketones through Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes
    Wu, Chao
    Liang, Zhiwu
    Yan, Dong
    He, Weimin
    Xiang, Jiannan
    SYNTHESIS-STUTTGART, 2013, 45 (18): : 2605 - 2611
  • [43] An Efficient [2+2+1] Synthesis of 2,5-Disubstituted Oxazoles via Gold-Catalyzed Intermolecular Alkyne Oxidation
    He, Weimin
    Li, Chaoqun
    Zhang, Liming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) : 8482 - 8485
  • [44] Gold-catalyzed alkyne-diol bicycloketalization enables enantioselective divergent total syntheses of attenols
    Shin, Ji Soo
    Lee, Jaeyeon
    Han, Sunkyu
    Lee, Hee-Yoon
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (21): : 5840 - 5844
  • [45] Gold-catalyzed alkyne hydroxylation:: Synthesis of 2-substituted benzo[b]furan compounds
    Zhang Yuan
    Xin Zhi-Jun
    Xue Ji-Jun
    Li Ying
    CHINESE JOURNAL OF CHEMISTRY, 2008, 26 (08) : 1461 - 1464
  • [46] A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals
    Tlais, Sami F.
    Dudley, Gregory B.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 570 - 577
  • [47] Efficient Synthesis of γ-Lactones via Gold-Catalyzed Tandem Cycloisomerization/Oxidation
    Shu, Chao
    Liu, Meng-Qi
    Sun, Yu-Zhe
    Ye, Long-Wu
    ORGANIC LETTERS, 2012, 14 (18) : 4958 - 4961
  • [48] Titania-Carbon Nitride Interfaces in Gold-Catalyzed CO Oxidation
    Jimenez-Calvo, Pablo
    Michel, Loic
    Keller, Valerie
    Caps, Valerie
    ACS APPLIED MATERIALS & INTERFACES, 2021, 13 (51) : 61015 - 61026
  • [49] Observing Initial Steps in Gold-Catalyzed Alkyne Transformations by Utilizing Bodipy-Tagged Phosphine-Gold Complexes
    Vasiuta, Roman
    Plenio, Herbert
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (18) : 6353 - 6360
  • [50] Generation of α-Imin Gold Carbenes through Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides
    Shu, Chao
    Wang, Yong-Heng
    Zhou, Bo
    Li, Xin-Ling
    Ping, Yi-Fan
    Lu, Xin
    Ye, Long-Wu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (30) : 9567 - 9570