Application of 1-(3-bromo-3,3-difluoroprop-1-ynyl)benzenes in Diels-Alder reactions:: Synthesis of ortho-CF2Br-substituted biaryls

被引:7
作者
Muzalevskiy, Vasilly M. [1 ]
Nenajdenko, Valentine G. [1 ]
Shastin, Aleksey V. [2 ]
Balenkova, Elizabeth S. [1 ]
Haufe, Guenter [3 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
[2] Inst Problems Chem Phys, Chernogolovka 142432, Moscow Region, Russia
[3] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源
SYNTHESIS-STUTTGART | 2008年 / 18期
关键词
alkynes; biaryls; bicyclic compounds; Diels-Alder reaction; fluorine;
D O I
10.1055/s-2008-1067221
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-(3-Bromo-3,3-difluoroprop-1-ynyl)benzenes were found to be good dienophiles in Diels-Alder reactions. Based oil this key reaction a new pathway towards biaryls with an ortho-CF2Br group was elaborated.
引用
收藏
页码:2899 / 2904
页数:6
相关论文
共 66 条
[1]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[2]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[3]  
Banks R.E., 1994, ORGANOFLUORINE CHEM
[4]   The properties of known drugs .1. Molecular frameworks [J].
Bemis, GW ;
Murcko, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (15) :2887-2893
[5]   Diels-Alder reactions of polyfluorinated 2,4-cyclohexadienones with α- and β-fluorostyrenes [J].
Bogachev, AA ;
Kobrina, LS ;
Meyer, OCJ ;
Haufe, G .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) :135-143
[6]   Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents [J].
Bringmann, G ;
Breuning, M ;
Tasler, S .
SYNTHESIS-STUTTGART, 1999, (04) :525-558
[7]  
Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis
[8]   Dienophilic reactivity of perfluoroalkenyl ketones in Diels-Alder reactions [J].
Chanteau, F ;
Essers, M ;
Plantier-Royon, R ;
Haufe, G ;
Portella, C .
TETRAHEDRON LETTERS, 2002, 43 (09) :1677-1680
[9]   Synthesis of ortho-perfluoroalkyl phenones from hemifluorinated enones as key building blocks [J].
Chanteau, Frederic ;
Plantier-Royon, Richard ;
Haufe, Guenter ;
Portella, Charles .
TETRAHEDRON, 2006, 62 (38) :9049-9053
[10]  
Corey E.J., 2002, ANGEW CHEM, V114, P1724, DOI DOI 10.1021/JACS.7B06567