Metal-Free Trifluoromethylation of Aromatic and Heteroaromatic Aldehydes and Ketones

被引:66
作者
Qiao, Yupu [1 ]
Si, Tuda [1 ]
Yang, Ming-Hsiu [1 ]
Altman, Ryan A. [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
基金
美国国家科学基金会;
关键词
CROSS-COUPLING REACTIONS; ONE-STEP SYNTHESIS; ORGANIC HALIDES; GEM-DIFLUOROOLEFINATION; 1,1-DIFLUORO OLEFINS; MEDICINAL CHEMISTRY; CARBONYL-COMPOUNDS; ARYLBORONIC ACIDS; CONVENIENT METHOD; FLUORINATION;
D O I
10.1021/jo501289v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ability to convert simple and common substrates into fluoroalkyl derivatives under mild conditions remains an important goal for medicinal and agricultural chemists. One representative example of a desirable transformation involves the conversion of aromatic and heteroaromatic ketones and aldehydes into aryl and heteroaryl beta,beta,beta-trifluoroethylarenes and -heteroarenes. The traditional approach for this net transformation involves stoichiometric metals and/or multistep reaction sequences that consume excessive time, material, and labor resources while providing low yields of products. To complement these traditional strategies, we report a one-pot metal-free decarboxylative procedure for accessing beta,beta,beta-trifluoroethylarenes and -heteroarenes from readily available ketones and aldehydes. This method features several benefits, including ease of operation, readily available reagents, mild reaction conditions, high functional-group compatibility, and scalability.
引用
收藏
页码:7122 / 7131
页数:10
相关论文
共 93 条
[1]  
[Anonymous], ORGANOFLUORINE CHEMI
[2]  
[Anonymous], 2008, BIOORGAN MED CHEM
[3]   Tamed Arene and Heteroarene Trifluoromethylation [J].
Besset, Tatiana ;
Schneider, Cedric ;
Cahard, Dominique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050
[4]   Synthesis and Optical and Electronic Properties of Core-Modified 21,23-Dithiaporphyrins [J].
Bromby, Ashley D. ;
Jansonius, Ryan P. ;
Sutherland, Todd C. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (04) :1612-1620
[5]   Sustainable Practices in Medicinal Chemistry: Current State and Future Directions [J].
Bryan, Marian C. ;
Dillon, Barry ;
Hamann, Lawrence G. ;
Hughes, Gregory J. ;
Kopach, Michael E. ;
Peterson, Emily A. ;
Pourashraf, Mehrnaz ;
Raheem, Izzat ;
Richardson, Paul ;
Richter, Daniel ;
Sneddon, Helen F. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (15) :6007-6021
[6]   REACTION OF TRIFLUOROMETHYL KETONES AND TRIALKYLPHOSPHINES [J].
BURTON, DJ ;
HERKES, FE ;
KLABUNDE, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (21) :5042-&
[7]   Fluorinated ylides and related compounds [J].
Burton, DJ ;
Yang, ZY ;
Qiu, WM .
CHEMICAL REVIEWS, 1996, 96 (05) :1641-1715
[8]  
Chang J., 2012, Patent, Patent No. [W02012062157 Al, 2012062157]
[9]   Recent Advances in Transition-Metal-Catalyzed Trifluoromethylation and Related Transformations [J].
Chen, Pinhong ;
Liu, Guosheng .
SYNTHESIS-STUTTGART, 2013, 45 (21) :2919-2939
[10]   METHYL-3-OXO-OMEGA-FLUOROSULFONYLPERFLUOROPENTANOATE - A VERSATILE TRIFLUOROMETHYLATING AGENT FOR ORGANIC HALIDES [J].
CHEN, QY ;
DUAN, JX .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (18) :1389-1391