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

被引:90
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 30 条
  • [11] Platinum(II)-Catalyzed Intermolecular [3+2] Cycloaddition of Propadienyl Silyl Ethers and Alkenyl Ethers
    Kusama, Hiroyuki
    Ebisawa, Masaru
    Funami, Hideaki
    Iwasawa, Nobuharu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (45) : 16352 - +
  • [12] Rhodium-Catalyzed [3+2] Annulation of Indoles
    Lian, Yajing
    Davies, Huw M. L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) : 440 - +
  • [13] Diversity in Gold- and Silver-Catalyzed Cycloisomerization of Epoxide-Alkyne Functionalities
    Lin, Guan-You
    Li, Chia-Wen
    Hung, Siao-Hua
    Liu, Rai-Shung
    [J]. ORGANIC LETTERS, 2008, 10 (21) : 5059 - 5062
  • [14] Palladium-Catalyzed Three-Component [3+2] Cycloaddition of Propargyl Trifluoroacetates, Ethylidene Malononitriles, and Allyltributylstannane
    Lu, Shirong
    Jin, Tienan
    Bao, Ming
    Yamamoto, Yoshinori
    [J]. ORGANIC LETTERS, 2010, 12 (04) : 864 - 866
  • [15] Mainetti E, 2002, ANGEW CHEM INT EDIT, V41, P2132, DOI 10.1002/1521-3773(20020617)41:12<2132::AID-ANIE2132>3.0.CO
  • [16] 2-S
  • [17] Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters
    Marco-Contelles, Jose
    Soriano, Elena
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) : 1350 - 1357
  • [18] Propargylic esters in gold catalysis: Access to diversity
    Marion, Nicolas
    Nolan, Steven P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (16) : 2750 - 2752
  • [19] Gold- and Platinum-Catalyzed Cycloisomerization of Enynyl Esters versus Allenenyl Esters: An Experimental and Theoretical Study
    Marion, Nicolas
    Lemiere, Gilles
    Correa, Andrea
    Costabile, Chiara
    Ramon, Ruben S.
    Moreau, Xavier
    de Fremont, Pierre
    Dahmane, Rim
    Hours, Alexandra
    Lesage, Denis
    Tabet, Jean-Claude
    Goddard, Jean-Philippe
    Gandon, Vincent
    Cavallo, Luigi
    Fensterbank, Louis
    Malacria, Max
    Nolan, Steven P.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (13) : 3243 - 3260
  • [20] Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids
    Miki, K
    Ohe, K
    Uemura, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) : 8505 - 8513