A novel catalytic process for trifluoromethylation of bromoaromatic compounds

被引:58
作者
Samant, Bhupesh S. [1 ]
Kabalka, George W. [2 ,3 ,4 ]
机构
[1] Rhodes Univ, Div Pharmaceut Chem, Fac Pharm, ZA-6140 Grahamstown, South Africa
[2] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
[3] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA
[4] UT Med Hosp, Biomed Imaging Ctr, Knoxville, TN 37920 USA
关键词
FORMING REDUCTIVE ELIMINATION; ASYMMETRIC FLUORINATION; AROMATIC-COMPOUNDS; RADICALS; AGENTS; COPPER;
D O I
10.1039/c1cc12098k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium-catalyzed trifluoromethylation of aryl bromides has been achieved in micellar media. The micellar conditions result in enhanced yields and are applicable to bromoaromatics with ketone, aldehyde, hydroxyl and amine functionalities.
引用
收藏
页码:7236 / 7238
页数:3
相关论文
共 52 条
[1]   Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].
Ball, Nicholas D. ;
Kampf, Jeff W. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+
[2]   Identification of 4,5-Dihydro-1H-pyrazolo[4,3-h]quinazoline Derivatives as a New Class of Orally and Selective Polo-Like Kinase 1 Inhibitors [J].
Beria, Italo ;
Ballinari, Dario ;
Bertrand, Jay Aaron ;
Borghi, Daniela ;
Bossi, Roberto Tiberio ;
Brasca, Maria Gabriella ;
Cappella, Paolo ;
Caruso, Michele ;
Ceccarelli, Walter ;
Ciavolella, Antonella ;
Cristiani, Cinzia ;
Croci, Valter ;
De Ponti, Anna ;
Fachin, Gabriele ;
Ferguson, Ronald Dale ;
Lansen, Jacqueline ;
Moll, Jurgen Karl ;
Pesenti, Enrico ;
Posteri, Helena ;
Perego, Rita ;
Rocchetti, Maurizio ;
Storici, Paola ;
Volpi, Daniele ;
Valsasina, Barbara .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (09) :3532-3551
[3]   REACTIONS OF TRIFLUOROMETHYL RADICALS .1. PHOTOCHEMICAL REACTIONS OF TRIFLUOROIODOMETHANE WITH BENZENE AND SOME HALOGENOBENZENES [J].
BIRCHALL, JM ;
IRVIN, GP ;
BOYSON, RA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (05) :435-439
[4]   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
[5]   The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].
Cho, Eun Jin ;
Senecal, Todd D. ;
Kinzel, Tom ;
Zhang, Yong ;
Watson, Donald A. ;
Buchwald, Stephen L. .
SCIENCE, 2010, 328 (5986) :1679-1681
[6]   THE DIRECT TRIFLUOROMETHYLATION OF ARYL CHLORIDES USING BURTON REAGENT [J].
CLARK, JH ;
MCCLINTON, MA ;
BLADE, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) :638-639
[7]  
Cottet F, 2003, EUR J ORG CHEM, V2003, P1559
[8]   Carbon-carbon bond-forming reductive elimination from arylpalladium complexes containing functionalized alkyl groups. Influence of ligand steric and electronic properties on structure, stability, and reactivity [J].
Culkin, DA ;
Hartwig, JF .
ORGANOMETALLICS, 2004, 23 (14) :3398-3416
[9]   Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes [J].
Dubinina, Galyna G. ;
Furutachi, Hideki ;
Vicic, David A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8600-+
[10]   ABSORPTION AND PROTON MAGNETIC-RESONANCE SPECTROSCOPIC INVESTIGATION OF ENVIRONMENT OF ACETOPHENONE AND BENZOPHENONE IN AQUEOUS MICELLAR SOLUTIONS [J].
FENDLER, JH ;
FENDLER, EJ ;
INFANTE, GA ;
SHIH, PS ;
PATTERSON, LK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (01) :89-95