Access toward Fluorenone Derivatives through Solvent-Free Ruthenium Trichloride Mediated [2+2+2] Cycloadditions

被引：29
|
作者：
Ye, Fei [1 ]
Haddad, Mansour [1 ]
Michelet, Veronique [1 ]
Ratovelomanana-Vidal, Virginie [1 ]
机构：
[1] PSL Res Univ, Chim ParisTech, CNRS, Inst Rech Chim Paris, F-75005 Paris, France
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 21期
关键词：
C-H ACTIVATION; PALLADIUM-CATALYZED CYCLOCARBONYLATION; FREE ORGANIC SYNTHESES; AZAFLUORENONE ALKALOIDS; SYNTHETIC APPLICATIONS; ARUNDINA-GRAMNIFOLIA; BENZOIC ANHYDRIDES; TRANSITION-METALS; HECK CYCLIZATION; ALDOXIME ETHERS;
D O I：
10.1021/acs.orglett.6b02840
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and practical route for the preparation of highly substituted fluorenones and analogues via solvent-free ruthenium trichloride mediated [2 + 2 + 2] cycloaddition of alpha,omega-diynes and alkynes has been developed. This green chemistry approach involves a solventless and atom-economical catalytic process to generate densely functionalized fluorenones and related derivatives of high synthetic utility.
引用
收藏
页码：5612 / 5615
页数：4
相关论文
共 50 条
  • [1] Solvent-free ruthenium trichloride-mediated [2+2+2] cycloaddition of α,ω-diynes and cyanamides: a convenient access to 2-aminopyridines
    Ye, Fei
    Haddad, Mansour
    Michelet, Veronique
    Ratovelomanana-Vidal, Virginie
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (06): : 1063 - 1068
  • [2] Cobalt-mediated [2+2+2] cycloadditions of pyrimidine derivatives to alkynes
    Pelissier, H
    Rodriguez, J
    Vollhardt, KPC
    CHEMISTRY-A EUROPEAN JOURNAL, 1999, 5 (12) : 3549 - 3561
  • [3] Intracellular Ruthenium-Promoted (2+2+2) Cycloadditions
    Miguel-Avila, Joan
    Tomas-Gamasa, Maria
    Mascarenas, Jose L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (40) : 17628 - 17633
  • [4] Dihydrobiphenylenes through Ruthenium-Catalyzed [2+2+2] Cycloadditions of ortho-Alkenylarylacetylenes with Alkynes
    Garcia-Rubin, Silvia
    Gonzalez-Rodriguez, Carlos
    Garcia-Yebra, Cristina
    Varela, Jesus A.
    Esteruelas, Miguel A.
    Saa, Carlos
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) : 1841 - 1844
  • [5] Solvent-Free Iridium(III)-Catalyzed [2+2+2] Cycloaddition Providing Access to Fused Arenes: Isoindolines, Dihydroisobenzofurans and Indanes
    Auvinet, Anne-Laure
    Michelet, Veronique
    Ratovelomanana-Vidal, Virginie
    SYNTHESIS-STUTTGART, 2013, 45 (14): : 2003 - 2008
  • [6] Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations
    Mallagaray, Alvaro
    Medina, Sandra
    Dominguez, Gema
    Perez-Castells, Javier
    SYNLETT, 2010, (14) : 2114 - 2118
  • [7] Syntheses of (+)-Complanadine A and Lycodine Derivatives by Regioselective [2+2+2] Cycloadditions
    Yuan, Changxia
    Chang, Chih-Tsung
    Siegel, Dionicio
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5647 - 5668
  • [8] A Quick Access to 1-(2-Pyridyl)indoles via Solvent-Free Ruthenium(II)-Catalyzed Chemo- and Regioselective [2+2+2] Cycloaddition of α,ω-Diynes and N-Cyanoindoles
    Chowdhury, Hrishikesh
    Goswami, Avijit
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (02) : 314 - 322
  • [9] COBALT MEDIATED [2+2+2]-CYCLOADDITIONS - A SIMPLE ROUTE TO SUBSTITUTED CYCLOPENTADIENONES
    GESING, ERF
    TANE, JP
    VOLLHARDT, KPC
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (12): : 1023 - 1024
  • [10] Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions
    Boñaga, LVR
    Zhang, HC
    Moretto, AF
    Ye, H
    Gauthier, DA
    Li, J
    Leo, GC
    Maryanoff, BE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) : 3473 - 3485
12345