Synthesis of α-Trifluoromethyl Ketones via the Cu-Catalyzed Trifluoromethylation of Silyl Enol Ethers Using an Electrophilic Trifluoromethylating Agent

被引:68
作者
Li, Lun [1 ]
Chen, Qing-Yun [1 ]
Guo, Yong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
RADICAL TRIFLUOROMETHYLATION; ASYMMETRIC FLUORINATION; PERFLUOROALKYLATION; CHEMISTRY; REAGENTS; CARBONYL; PALLADIUM; EFFICIENT; RHODIUM; ARENE;
D O I
10.1021/jo500713f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method has been developed for the synthesis of alpha-trifluoromethyl ketones via the Cu-catalyzed trifluoromethylation of silyl enol ethers with an electrophilic trifluoromethylating agent, which produces a trifluoromethyl radical.
引用
收藏
页码:5145 / 5152
页数:8
相关论文
共 77 条
[1]   The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes [J].
Allen, Anna E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) :4986-+
[2]   Recent Progress in Catalytic Aromatic Trifluoromethylation [J].
Amii, Hideki .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (07) :752-762
[3]   Building up the trifluoromethyl group:: A new synthesis of α-trifluoromethylketones. [J].
Anselmi, E ;
Blazejewski, JC ;
Wakselman, C .
TETRAHEDRON LETTERS, 1998, 39 (52) :9651-9654
[4]   Tamed Arene and Heteroarene Trifluoromethylation [J].
Besset, Tatiana ;
Schneider, Cedric ;
Cahard, Dominique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050
[5]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895
[6]   Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].
Bouchy, A ;
Rinaldi, D ;
Rivail, JL .
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281
[7]   Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones [J].
Deb, Arghya ;
Manna, Srimanta ;
Modak, Atanu ;
Patra, Tuhin ;
Maity, Soham ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9747-9750
[8]   Fluorinated high-performance polymers: Poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups [J].
Dhara, Mahua G. ;
Banerjee, Susanta .
PROGRESS IN POLYMER SCIENCE, 2010, 35 (08) :1022-1077
[9]   Nucleophilic Trifluoromethylation of C=N Bonds [J].
Dilman, Alexander D. ;
Levin, Vitalij V. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) :831-841
[10]   Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation [J].
Eisenberger, P ;
Gischig, S ;
Togni, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2579-2586