High-Pressure-Promoted Multicomponent and Metal-Free Synthesis of Polyfunctionalized Biaryls

被引:15
作者
Minuti, Lucio [1 ]
Piazzolla, Francesca [2 ]
Temperini, Andrea [2 ]
机构
[1] Univ Perugia, Dipartimento Chim Biol & Biotecnol, Via Elce Sotto 8, I-06123 Perugia, Italy
[2] Univ Perugia, Dipartimento Chim & Tecnol Farmaco, Via Liceo 1, I-06123 Perugia, Italy
关键词
Multicomponent reactions; High-pressure chemistry; Acylation; Cycloaddition; Biaryls; DIELS-ALDER APPROACH; PRIVILEGED STRUCTURES; ELLAGIC ACID; DISCOVERY; CATALYST; ACCESS; AMINES; AGENT; METABOLISM; ANALOGS;
D O I
10.1002/ejoc.201700898
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and metal-free synthesis of biaryls and heterobiaryls has been developed through a key three-component reaction involving benzylideneacetones, isopropenyl acetate and methyl propiolate under high pressure (9 kbar) and mild reaction temperatures (40 degrees C). The described synthetic protocol provides rapid access to novel, highly functionalized and metal-uncontamined 1,1-biaryls and heterobiaryls in an energy- and step-economic fashion.
引用
收藏
页码:5370 / 5377
页数:8
相关论文
共 89 条
  • [21] A Radical Process towards the Development of Transition-Metal-Free Aromatic Carbon-Carbon Bond-Forming Reactions
    Chan, Tek Long
    Wu, Yinuo
    Choy, Pui Ying
    Kwong, Fuk Yee
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (47) : 15802 - 15814
  • [22] Benzofurans as Efficient Dienophiles in Normal Electron Demand [4+2] Cycloadditions
    Chopin, Nathalie
    Gerard, Helene
    Chataigner, Isabelle
    Piettre, Serge R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) : 1237 - 1246
  • [23] Clayden J., 2009, Angew. Chem, V121, P6516
  • [24] The Challenge of Atropisomerism in Drug Discovery
    Clayden, Jonathan
    Moran, Wesley J.
    Edwards, Paul J.
    LaPlante, Steven R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) : 6398 - 6401
  • [25] Corey E. J., 2010, Enantioselective Chemical Synthesis: Methods, Logic and Practice
  • [26] Sol-gel chemistry in medicinal science
    Coradin, T
    Boissière, M
    Livage, J
    [J]. CURRENT MEDICINAL CHEMISTRY, 2006, 13 (01) : 99 - 108
  • [27] desMeijere A., 2004, METAL CATALYZED CROS
  • [28] DISC-LIKE MESOGEN POLYMORPHISM
    DESTRADE, C
    FOUCHER, P
    GASPAROUX, H
    TINH, NH
    LEVELUT, AM
    MALTHETE, J
    [J]. MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1984, 106 (1-2) : 121 - 146
  • [29] Excited State and Injection Dynamics of Triphenylamine Sensitizers Containing a Benzothiazole Electron-Accepting Group on TiO2 and Al2O3 Thin Films
    Fakis, Mihalis
    Hrobarik, Peter
    Yushchenko, Oleksandr
    Sigmundova, Ivica
    Koch, Marius
    Rosspeintner, Arnulf
    Stathatos, Elias
    Vauthey, Eric
    [J]. JOURNAL OF PHYSICAL CHEMISTRY C, 2014, 118 (49) : 28509 - 28519
  • [30] Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction
    Feng, Xing-Wen
    Li, Chao
    Wang, Na
    Li, Kun
    Zhang, Wei-Wei
    Wang, Zao
    Yu, Xiao-Qi
    [J]. GREEN CHEMISTRY, 2009, 11 (12) : 1933 - 1936