Visible-light-promoted and photocatalyst-free trifluoromethylation of enamides

被引：64
作者：
Wang, Hao
Cheng, Yuanzheng
Yu, Shouyun [1 ]
机构：
[1] State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China
来源：
SCIENCE CHINA-CHEMISTRY | 2016年 / 59卷 / 02期
基金：
中国国家自然科学基金;
关键词：
enamide; photochemistry; visible light; trifluoromethylation; radical; CATALYZED ENANTIOSELECTIVE HYDROGENATION; TRANSITION-METAL-COMPLEXES; PHOTOREDOX CATALYSIS; ORGANIC-SYNTHESIS; NUCLEOPHILES; CHEMISTRY; ALDEHYDES; FLUORINE; AMINO; ACID;
D O I：
10.1007/s11426-015-5528-1
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and practical method is developed for the trifluoromethylation of enamides using Umemoto's reagent as the trifluoromethylating reagent. These reactions proceeded under visible light irradiation without any photocatalyst at room temperature in good chemical yields.
引用
收藏
页码：195 / 198
页数：4
相关论文
共 33 条
[1]  
Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/NCHEM.1727, 10.1038/nchem.1727]
[2]   Catalytic asymmetric Michael reactions with enamides as nucleophiles [J].
Berthiol, Florian ;
Matsubara, Ryosuke ;
Kawai, Nobuyuki ;
Kobayashi, Shu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) :7803-7805
[3]   Gold Catalysis Coupled with Visible Light Stimulation: Syntheses of Functionalized Indoles [J].
Cai, Shunyou ;
Yang, Kai ;
Wang, David Zhigang .
ORGANIC LETTERS, 2014, 16 (10) :2606-2609
[4]   Enamides: valuable organic substrates [J].
Carbery, David R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460
[5]   Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates [J].
Carboni, Aude ;
Dagousset, Guillaume ;
Magnier, Emmanuel ;
Masson, Geraldine .
ORGANIC LETTERS, 2014, 16 (04) :1240-1243
[6]   Enantioselective Direct α-Annination of Aldehydes via a Photoredox Mechanism: A Strategy for Asymmetric Amine Fragment Coupling [J].
Cecere, Giuseppe ;
Koenig, Christian M. ;
Alleva, Jennifer L. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (31) :11521-11524
[7]   Regiospecific Synthesis of 1-Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion [J].
Cheng, Yuanzheng ;
Yuan, Xiangai ;
Jiang, Heng ;
Wang, Ruzhi ;
Ma, Jing ;
Zhang, Yan ;
Yu, Shouyun .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) :2859-2866
[8]   Salicylihalamides A and B, novel cytotoxic macrolides from the marine sponge Haliclona sp. [J].
Erickson, KL ;
Beutler, JA ;
Cardellina, JH ;
Boyd, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8188-8192
[9]   Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature [J].
Feng, Chao ;
Loh, Teck-Peng .
CHEMICAL SCIENCE, 2012, 3 (12) :3458-3462
[10]   Use of Nonfunctionalized Enamides and Enecarbamates in Asymmetric Synthesis [J].
Gopalaiah, Kovuru ;
Kagan, Henri B. .
CHEMICAL REVIEWS, 2011, 111 (08) :4599-4657
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