Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines

被引:179
作者
Egami, Hiromichi [1 ,2 ]
Kawamura, Shintaro [1 ,2 ]
Miyazaki, Ayako [1 ,2 ]
Sodeoka, Mikiko [1 ,2 ,3 ]
机构
[1] RIKEN, Synthet Organ Chem Lab, Wako, Saitama 3510198, Japan
[2] Japan Sci & Technol Agcy, Sodeoka Live Cell Chem Project, ERATO, Wako, Saitama 3510198, Japan
[3] RIKEN Ctr Sustainable Resource Sci, Wako, Saitama 3510198, Japan
关键词
amines; aziridines; copper; multicomponent reactions; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; TERMINAL ALKENES; FLUORINE; EFFICIENT; OXYTRIFLUOROMETHYLATION; HYDROTRIFLUOROMETHYLATION; ALLYLSILANES; REAGENTS;
D O I
10.1002/anie.201303350
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A multitalented system: N-Migratory oxytrifluoromethylation and one-pot three-component reactions of allylamines as well as the aminotrifluoromethylation of alkenyl amines all proceeded efficiently in the presence of the Togni reagent (1) and CuI to afford a variety of β-trifluoromethylamine derivatives (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7841 / 7844
页数:4
相关论文
共 83 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]  
[Anonymous], 2005, ANGEW CHEM
[4]  
[Anonymous], 2009, Angew. Chem., Int. Ed.
[5]  
[Anonymous], 2006, ANGEW CHEM, V118, P4305
[6]  
[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1135/CCCC2011078
[7]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[8]   Using Fluorine Nuclear Magnetic Resonance To Probe the Interaction of Membrane-Active Peptides with the Lipid Bilayer [J].
Buer, Benjamin C. ;
Chugh, Jeetender ;
Al-Hashimi, Hashim M. ;
Marsh, E. Neil G. .
BIOCHEMISTRY, 2010, 49 (27) :5760-5765
[9]   Helix propensity of highly fluorinated amino acids [J].
Chiu, Hsien-Po ;
Suzuki, Yuta ;
Gullickson, Donald ;
Ahmad, Raheel ;
Kokona, Bashkim ;
Fairman, Robert ;
Cheng, Richard P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15556-15557
[10]   Effect of Highly Fluorinated Amino Acids on Protein Stability at a Solvent-Exposed Position on an Internal Strand of Protein G B1 Domain [J].
Chiu, Hsien-Po ;
Kokona, Bashkim ;
Fairman, Robert ;
Cheng, Richard P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (37) :13192-13193