Platinum(II)-Catalyzed Generation and [3+2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds

被引:89
|
作者
Saito, Kodai [1 ]
Sogou, Hideyuki [1 ]
Suga, Takuya [1 ]
Kusama, Hiroyuki [1 ]
Iwasawa, Nobuharu [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
关键词
CATALYZED CYCLOISOMERIZATION; PLATINUM CATALYSIS; PROPARGYLIC ESTERS; GOLD CATALYSIS; ENYNYL ESTERS; CYCLOPROPANATION; CARBOCYCLES; DIVERSITY; INDOLE;
D O I
10.1021/ja108586d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pt(II)-catalyzed generation of unsaturated carbene complex intermediates from various propargyl ether derivatives based on electrophilic activation of alkynes was realized. These in situ generated unsaturated carbene complexes undergo [3+2] cycloaddition reaction with various vinyl ethers, leading to efficient formation of indoles, naphthols, and benzofuran fused with a five-membered ring in high yields.
引用
收藏
页码:689 / 691
页数:3
相关论文
共 50 条
  • [31] Cu-catalyzed Asymmetric Dearomative [3+2] Cycloaddition Reaction of Benzazoles with Aminocyclopropanes
    Zhang, Meng-Cheng
    Wang, Dong-Chao
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Guo, Hai-Ming
    You, Shu-Li
    CHEM, 2019, 5 (01): : 156 - 167
  • [32] [3+2] Cycloaddition Reaction of Cyclopropyl Ketones with Alkynes Catalyzed by Nickel/Dimethylaluminum Chloride
    Tamaki, Takashi
    Ohashi, Masato
    Ogoshi, Sensuke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12067 - 12070
  • [33] Palladium-catalyzed bisdiene carbocyclizations: A facile [3+2] cycloaddition reaction mode
    Takacs, JM
    Leonov, AP
    ORGANIC LETTERS, 2003, 5 (23) : 4317 - 4320
  • [34] Cooperative Catalysis for the First Asymmetric Formal [3+2] Cycloaddition Reaction of Isocyanoacetates to α,β-Unsaturated Ketones
    Arroniz, Carlos
    Gil-Gonzalez, Alberto
    Semak, Vladislav
    Escolano, Carmen
    Bosch, Joan
    Amat, Mercedes
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) : 3755 - 3760
  • [35] A chiral cobalt(II) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines
    Ma, Baiwei
    Luo, Weiwei
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2017, 53 (29) : 4077 - 4079
  • [36] Chiral nickel(II) complex catalyzed asymmetric (3+2) cycloaddition of α-diazo pyrazoleamides with 2-siloxy-1-alkenes
    Yang, Wei
    Yang, Zhendong
    Chen, Long
    Lu, Yican
    Zhang, Cefei
    Su, Zhishan
    Liu, Xiaohua
    Feng, Xiaoming
    CHINESE CHEMICAL LETTERS, 2023, 34 (04)
  • [37] Iodide-Mediated [3+2]-Cycloaddition Reaction with N-Tosylaziridines and α,β-Unsaturated Ketones
    Nakagawa, Yuya
    Yamaguchi, Keigo
    Hosokawa, Seijiro
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7787 - 7796
  • [38] Dirhodium(II)-catalyzed [3+2] cycloaddition of N-arylaminocyclopropane with alkyne derivatives
    Liu, Wentong
    Kuang, Yi
    Wang, Zhifan
    Zhu, Jin
    Wang, Yuanhua
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 542 - 550
  • [39] Zn(II)-catalyzed asymmetric [3+2] cycloaddition of acyclic enones with azomethine ylides
    Kumar, Sundaravel Vivek
    Olusegun, Jeremiah
    Guiry, Patrick J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (35)
  • [40] Tin(II) Chloride Catalyzed Multicomponent Synthesis of Propargylamines and Intramolecular [3+2] Cycloaddition
    Afraj, Shakil N.
    Chen, Chinpiao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (02) : 257 - 263