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
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 36期
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
[1]   Synthesis, characterization, theoretical, anti-bacterial and molecular docking studies of quinoline based chalcones as a DNA gyrase inhibitor [J].
Abdullah, Muhammad Imran ;
Mahmood, Asif ;
Madni, Murtaza ;
Masood, Sara ;
Kashif, Muhammad .
BIOORGANIC CHEMISTRY, 2014, 54 :31-37
[2]   Thermally, Operationally, and Environmentally Stable Organic Thin-Film Transistors Based on Bis[1]benzothieno[2,3-d:2′,3′-d′]naphtho[2,3-b:6,7-b′]dithiophene Derivatives: Effective Synthesis, Electronic Structures, and Structure-Property Relationship [J].
Abe, Masahiro ;
Mori, Takamichi ;
Osaka, Itaru ;
Sugimoto, Kunihisa ;
Takimiya, Kazuo .
CHEMISTRY OF MATERIALS, 2015, 27 (14) :5049-5057
[3]   Open analogues of arcyriaflavin A.: Synthesis through Diels-Alder reaction between maleimides and 1-aryl-3-tert-butyldimethylsiloxy-1,3-butadienes [J].
Adeva, M ;
Sahagún, H ;
Caballero, E ;
de Clairac, RPL ;
Medarde, M ;
Tomé, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3387-3394
[4]  
ASHBURN BO, 2006, ANGEW CHEM, V118, P6889
[5]   Diels-Alder approach to biaryls: Elucidation of competing tandem [2+2] cycloaddition/[1,3] sigmatropic shift pathway [J].
Ashburn, Bradley O. ;
Carter, Rich G. ;
Zakharov, Lev N. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (18) :7305-7309
[6]   A Diels-Alder approach to biaryls (DAB): synthesis of the western portion of TMC-95 [J].
Ashburn, Bradley O. ;
Rathbone, Lauren K. ;
Camp, Elizabeth H. ;
Carter, Rich G. .
TETRAHEDRON, 2008, 64 (05) :856-865
[7]   Diels-Alder approach to tetra-ortho-substituted biaryls employing propargylic tertiary alcohols as dienophiles [J].
Ashburn, Bradley O. ;
Carter, Rich G. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10220-10223
[8]   Synthesis of tetra-ortho-substituted, phosphorus-containing and carbonyl-containing biaryls utilizing a diels-alder approach [J].
Ashburn, Bradley O. ;
Carter, Rich G. ;
Zakharov, Lev N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (29) :9109-9116
[9]   Diels-Alder approach to polysubstituted biaryls: Rapid entry to tri- and tetra-ortho-substituted phosphorus-containing biaryls [J].
Ashburn, Bradley O. ;
Carter, Rich G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6737-6741
[10]   High-Pressure Diels-Alder Cycloadditions between Benzylideneacetones and 1,3-Butadienes: Application to the Synthesis of (R,R)-(-)- and (S,S)-(+)-Δ8-Tetrahydrocannabinol [J].
Ballerini, Eleonora ;
Minuti, Lucio ;
Piermatti, Oriana .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) :4251-4260
123456789