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 [J].
Chan, Tek Long ;
Wu, Yinuo ;
Choy, Pui Ying ;
Kwong, Fuk Yee .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (47) :15802-15814
[22]   Benzofurans as Efficient Dienophiles in Normal Electron Demand [4+2] Cycloadditions [J].
Chopin, Nathalie ;
Gerard, Helene ;
Chataigner, Isabelle ;
Piettre, Serge R. .
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 [J].
Clayden, Jonathan ;
Moran, Wesley J. ;
Edwards, Paul J. ;
LaPlante, Steven R. .
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 [J].
Coradin, T ;
Boissière, M ;
Livage, J .
CURRENT MEDICINAL CHEMISTRY, 2006, 13 (01) :99-108
[27]  
desMeijere A., 2004, METAL CATALYZED CROS
[28]   DISC-LIKE MESOGEN POLYMORPHISM [J].
DESTRADE, C ;
FOUCHER, P ;
GASPAROUX, H ;
TINH, NH ;
LEVELUT, AM ;
MALTHETE, 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 [J].
Fakis, Mihalis ;
Hrobarik, Peter ;
Yushchenko, Oleksandr ;
Sigmundova, Ivica ;
Koch, Marius ;
Rosspeintner, Arnulf ;
Stathatos, Elias ;
Vauthey, Eric .
JOURNAL OF PHYSICAL CHEMISTRY C, 2014, 118 (49) :28509-28519
[30]   Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction [J].
Feng, Xing-Wen ;
Li, Chao ;
Wang, Na ;
Li, Kun ;
Zhang, Wei-Wei ;
Wang, Zao ;
Yu, Xiao-Qi .
GREEN CHEMISTRY, 2009, 11 (12) :1933-1936