Three-Component Gold(I)-Catalyzed Alkoxyvinylation

被引:1
|
作者
Hammarback, L. Anders [1 ]
Medina-Gil, Tania [1 ,2 ]
Sadurni, Anna [1 ]
Echavarren, Antonio M. [1 ,2 ]
机构
[1] Barcelona Inst Sci & Technol BIST, Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[2] Univ Rovira & Virgili URV, Dept Quim Organ & Anal, Tarragona 43007, Spain
基金
欧洲研究理事会;
关键词
INTERMOLECULAR 2+2 CYCLOADDITION; GOLD; ACETYLENE;
D O I
10.1021/acs.orglett.4c02102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acetylene has been underexploited despite being a highly valuable feedstock for chemical synthesis. We have developed the first true gold(I)-catalyzed intermolecular three-component reaction between acetylene, alkenes, and alcohols to afford beta-vinyl hemiaminal scaffolds from N-vinyl amides. Unusual biscyclopropyl and 3-vinyl N-heterocyclic scaffolds were obtained through the incorporation of a second N-vinyl unit or tethered alkene into the starting material.
引用
收藏
页码:6375 / 6379
页数:5
相关论文
共 50 条
  • [1] Gold-Catalyzed Three-Component Coupling: Oxidative Oxyarylation of Alkenes
    Melhado, Asa D.
    Brenzovich, William E., Jr.
    Lackner, Aaron D.
    Toste, F. Dean
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (26) : 8885 - +
  • [2] Synthesis of substituted anilinesviaa gold-catalyzed three-component reaction
    Ueda, Hirofumi
    Yamamoto, Ryota
    Yamaguchi, Minami
    Tokuyama, Hidetoshi
    Organic and Biomolecular Chemistry, 2021, 19 (04): : 765 - 769
  • [3] Heterogeneous gold(I)-catalyzed three-component reaction of aldehydes, alkynes, and orthoformates toward propargyl ethers
    Zeng, Jiajun
    Yi, Feiyan
    Cai, Mingzhong
    SYNTHETIC COMMUNICATIONS, 2020, 50 (13) : 1936 - 1945
  • [4] Synthesis of polysubstituted pyrroles via a gold(I)-catalyzed tandem three-component reaction at room temperature
    Li, Li
    Chen, Qi
    Xiong, Xiaonan
    Zhang, Chuang
    Qian, Jingjing
    Shi, Jie
    An, Qiong
    Zhang, Ming
    CHINESE CHEMICAL LETTERS, 2018, 29 (12) : 1893 - 1896
  • [5] Synthesis of substituted anilines via a gold-catalyzed three-component reaction
    Ueda, Hirofumi
    Yamamoto, Ryota
    Yamaguchi, Minami
    Tokuyama, Hidetoshi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (04) : 765 - 769
  • [6] Cu(I)-Catalyzed Three-Component Cyclization for the Construction of Functionalized Thiazoles
    Wang, Yajun
    Liu, Xiang
    Zhu, Baofu
    Guo, Pengfeng
    Pei, Yongyan
    He, Qiuxing
    Cao, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15): : 10118 - 10124
  • [7] I2-Catalyzed three-component protocol for the synthesis of quinazolines
    Panja, Sumit Kumar
    Dwivedi, Nidhi
    Saha, Satyen
    TETRAHEDRON LETTERS, 2012, 53 (46) : 6167 - 6172
  • [8] Enantioselective, copper(I)-catalyzed three-component reaction for the preparation of propargylamines
    Gommermann, N
    Koradin, X
    Polborn, K
    Knochel, P
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) : 5763 - 5766
  • [9] Gold(III)-Catalyzed Three-Component Coupling Reaction (TCC) Selective toward Furans
    Li, Jian
    Liu, Li
    Ding, Dong
    Sun, Jiangtao
    Ji, Yangxuan
    Dong, Jialing
    ORGANIC LETTERS, 2013, 15 (11) : 2884 - 2887
  • [10] A convergent synthesis of vinyloxyimidazopyridine via Cu(I)-catalyzed three-component coupling
    Samanta, Sadhanendu
    Mondal, Susmita
    Hajra, Alakananda
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (07) : 1088 - 1092