A Facile Parallel Synthesis of Trifluoroethyl-Substituted Alkynes

被引:125
作者
Liu, Cui-Bo [1 ]
Meng, Wei [1 ]
Li, Feng [1 ]
Wang, Shuai [1 ]
Nie, Jing [1 ]
Ma, Jun-An [1 ]
机构
[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
关键词
alkynes; cross-coupling; diazo compounds; homogeneous catalysis; trifluoroethylation; ION CATALYZED HOMOLOGATION; CYCLOADDITION REACTIONS; MEDICINAL CHEMISTRY; DIAZOACETIC ESTERS; 2,2,2-TRIFLUORODIAZOETHANE; TRIFLUOROMETHYLATION; FLUORINATION; KETONES; ACID; PERFLUOROALKYLATION;
D O I
10.1002/anie.201202372
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Trifluoroethylation made easy: The ease of execution of the reaction (see scheme), which runs under mild conditions and without the need for additional base or ligands, allows for the rapid parallel synthesis of a broad variety of trifluoroethylated alkynes. Both experimental and theoretical analyses indicate that the trifluoromethylcarbene could undergo concerted insertion into the C sp-H bond of the alkyne. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6227 / 6230
页数:4
相关论文
共 67 条
[1]  
[Anonymous], 2004, ANGEW CHEM
[2]  
[Anonymous], 2005, ANGEW CHEM
[3]   INSERTION REACTIONS OF TRIFLUOROMETHYLCARBENE [J].
ATHERTON, JH ;
FIELDS, R .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (18) :2276-&
[4]   CYCLOADDITION REACTIONS OF 2,2,2-TRIFLUORODIAZOETHANE [J].
ATHERTON, JH ;
FIELDS, R .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (12) :1507-&
[5]   A short and efficient synthesis of 3-[2,2,2-trifluoroethyl]hexahydro-2H-1,4-diazepin-2-one [J].
Balsells, Jaume ;
Waters, Marjorie ;
Hansen, Karl ;
Kieczykowski, Gerard R. ;
Song, Zhiguo J. .
SYNTHESIS-STUTTGART, 2007, (18) :2779-2781
[6]   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
[7]   A family of highly active copper(I)-homoscorpionate catalysts for the alkyne cyclopropenation reaction [J].
Díaz-Requejo, MM ;
Mairena, MA ;
Belderrain, TR ;
Nicasio, MC ;
Trofimenko, S ;
Pérez, PJ .
CHEMICAL COMMUNICATIONS, 2001, (18) :1804-1805
[8]  
Doyle M. P., 1998, MODERN CATALYTIC MET
[9]   Stereoselectivity in metal carbene addition to a carbon-carbon triple bond tied to the reactant diazoacetate through a chiral linker [J].
Doyle, Michael P. ;
Weathers, Thomas M., Jr. ;
Wang, Yuanhua .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2403-2409
[10]   CARBENE CHEMISTRY .1. REACTIONS OF FLUOROALKYLDIAZO-COMPOUNDS [J].
FIELDS, R ;
HASZELDINE, RN .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :1881-&