An Efficient Route to Difluoromethylated Pyridines

被引:43
作者
Fujikawa, Kenichi [1 ]
Kobayashi, Akira [1 ]
Amii, Hideki [1 ]
机构
[1] Gunma Univ, Grad Sch Engn, Dept Chem & Chem Biol, Kiryu, Gunma 3768515, Japan
来源
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 19期
关键词
fluorine; pyridines; copper; catalysis; cross-coupling; decarboxylations; COPPER; DITHIOPYR; ARYL; TRIFLUOROMETHYLATION; DEFLUORINATION;
D O I
10.1055/s-0032-1316761
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient route to difluoromethylated pyridines was developed that involves copper-promoted cross-coupling of halopyridines with ethyl difluoro(trimethylsilyl)acetate and subsequent decarboxylation.
引用
收藏
页码:3015 / 3018
页数:4
相关论文
共 47 条
[21]   Non-acidic pyrazole EP1 receptor antagonists with in vivo analgesic efficacy [J].
Hall, Adrian ;
Billinton, Andy ;
Brown, Susan H. ;
Clayton, Nicholas M. ;
Chowdhury, Anita ;
Giblin, Gerard M. P. ;
Goldsmith, Paul ;
Hayhow, Thomas G. ;
Hurst, David N. ;
Kilford, Ian R. ;
Naylor, Alan ;
Passingham, Barry ;
Winyard, Lisa .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (11) :3392-3399
[22]  
Hiyama T., 2013, ORGANOFLUORINE COMPO
[23]   Selective difluoromethylation and monofluoromethylation reactions [J].
Hu, Jinbo ;
Zhang, Wei ;
Wang, Fei .
CHEMICAL COMMUNICATIONS, 2009, (48) :7465-7478
[24]   A general strategy for the synthesis of difluoromethyl-containing pyrazoles, pyridines and pyrimidines [J].
Iaroshenko, Viktor O. ;
Specowius, Verena ;
Vlach, Katharina ;
Vilches-Herrera, Marcelo ;
Ostrovskyi, Dmytro ;
Mkrtchyan, Satenik ;
Villinger, Alexander ;
Langer, Peter .
TETRAHEDRON, 2011, 67 (31) :5663-5677
[25]  
Katsuyama I, 1997, SYNLETT, P591
[26]  
Kirsch P., 2013, Modern Fluoroorganic Chemistry
[27]   Copper-Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives [J].
Kondo, Hideaki ;
Oishi, Masahiro ;
Fujikawa, Kenichi ;
Amii, Hideki .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) :1247-1252
[28]   Orally efficacious thrombin inhibitors with cyanofluorophenylacetamide as the P2 motif [J].
Kreutter, Kevin D. ;
Lu, Tianbao ;
Lee, Lily ;
Giardino, Edward C. ;
Patel, Sharmila ;
Huang, Hui ;
Xu, Guozhang ;
Fitzgerald, Mark ;
Haertlein, Barbara J. ;
Mohan, Venkatraman ;
Crysler, Carl ;
Eisennagel, Stephen ;
Dasgupta, Malini ;
McMillan, Martin ;
Spurlino, John C. ;
Huebert, Norman D. ;
Maryanoff, Bruce E. ;
Tomczuk, Bruce E. ;
Damiano, Bruce P. ;
Player, Mark R. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (09) :2865-2870
[29]  
Kuduk S. D., 2011, WO Pat., Patent No. 2011084371
[30]  
Lee L. F., 1985, Fur. Pat. Appl., Patent No. [0133612, EP 0133612]