One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis

被引：102
作者：
Carboni, Aude [1 ]
Dagousset, Guillaume [1 ]
Magnier, Emmanuel [2 ]
Masson, Geraldine [1 ]
机构：
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
[2] Univ Versailles St Quentin, UMR 8180, Inst Lavoisier Versailles, F-78035 Versailles, France
来源：
CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 91期
关键词：
VISIBLE-LIGHT PHOTOCATALYSIS; C-H TRIFLUOROMETHYLATION; CHIRAL PHOSPHORIC-ACID; BOND FORMATION; ELECTROPHILIC TRIFLUOROMETHYLATION; SODIUM TRIFLUOROMETHANESULFINATE; MEDIATED TRIFLUOROMETHYLATION; UNACTIVATED ALKENES; ORGANIC-SYNTHESIS; CONSTRUCTION;
D O I：
10.1039/c4cc07066f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report herein the first photoredox-catalyzed intermolecular aryl- and heteroaryltrifluoromethylation of alkenes. Under the optimized conditions using Umemoto's reagent as a CF3 source, a wide range of styrenes can be readily difunctionalized, affording the corresponding trifluoromethylated adducts in up to 99% yield.
引用
收藏
页码：14197 / 14200
页数：4
相关论文
共 93 条
[1]   Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts [J].
Alix, Aurelien ;
Lalli, Claudia ;
Retailleau, Pascal ;
Masson, Geraldine .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10389-10392
[2]  
[Anonymous], CHEM HETEROCYCLIC CO
[3]   Metal-Free Dioxygenation of Enecarbamates Mediated by a Hypervalent Iodine Reagent [J].
Bekkaye, Mathieu ;
Su, Yingpeng ;
Masson, Geraldine .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (19) :3978-3982
[4]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895
[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]  
Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/nchem.256, 10.1038/NCHEM.256]
[7]   Vaccinia Virus Virulence Factor N1L is a Novel Promising Target for Antiviral Therapeutic Intervention [J].
Cheltsov, Anton V. ;
Aoyagi, Mika ;
Aleshin, Alexander ;
Yu, Eric Chi-Wang ;
Gilliland, Taylor ;
Zhai, Dayong ;
Bobkov, Andrey A. ;
Reed, John C. ;
Liddington, Robert C. ;
Abagyan, Ruben .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (10) :3899-3906
[8]  
Chen P., 2013, SYNTHESIS-STUTTGART, P2919
[9]   Copper-Catalyzed Tandem Trifluoromethylation/Semipinacol Rearrangement of Allylic Alcohols [J].
Chen, Zhi-Min ;
Bai, Wei ;
Wang, Shao-Hua ;
Yang, Bin-Miao ;
Tu, Yong-Qiang ;
Zhang, Fu-Min .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9781-9785
[10]   Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction [J].
Courant, Thibaut ;
Masson, Geraldine .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) :423-427
12345678910