Metal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis

被引：128
作者：
Noto, Naoki [1 ]
Koike, Takashi [1 ]
Akita, Munetaka [1 ]
机构：
[1] Tokyo Inst Technol, Inst Innovat Res, Lab Chem & Life Sci, Midori Ku, R1-27,4259 Nagatsuta Cho, Yokohama, Kanagawa 2268503, Japan
来源：
CHEMICAL SCIENCE | 2017年 / 8卷 / 09期
关键词：
FLUOROALKYLATION REACTIONS; RADICAL POLYMERIZATION; TRIFLUOROMETHYLATION; DRIVEN; EFFICIENT; OXYDIFLUOROMETHYLATION; DIFUNCTIONALIZATION;
D O I：
10.1039/c7sc01703k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Regioselective amino-difluoromethylation of aromatic alkenes via C(sp(3))-CF2H and C(sp(3))-N bond formation with the C=C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, S-difluoromethyl-S-di(p-xylyl) sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermore, this noble metal-free protocol allows for the photocatalytic trifluoromethylation of alkenes.
引用
收藏
页码：6375 / 6379
页数：5
相关论文
共 49 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]   Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols [J].
Arai, Yusuke ;
Tomita, Ren ;
Ando, Gaku ;
Koike, Takashi ;
Akita, Munetaka .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) :1262-1265
[3]   Photocatalytic fluoroalkylation reactions of organic compounds [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio M. ;
Postigo, Al .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) :11153-11183
[4]   Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers [J].
Belhomme, Marie-Charlotte ;
Besset, Tatiana ;
Poisson, Thomas ;
Pannecoucke, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (37) :12836-12865
[5]  
Berberan-Santos MN., 2012, MOL FLUORESCENCE, DOI DOI 10.1002/9783527650002
[6]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[7]   Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis [J].
Chatterjee, Tanmay ;
Iqbal, Naeem ;
You, Youngmin ;
Cho, Eun Jin .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2284-2294
[8]   Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups [J].
Egami, Hiromichi ;
Sodeoka, Mikiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) :8294-8308
[9]   Photochemistry and photophysics of coordination compounds: Iridium [J].
Flamigni, Lucia ;
Barbieri, Andrea ;
Sabatini, Cristiana ;
Ventura, Barbara ;
Barigelletti, Francesco .
PHOTOCHEMISTRY AND PHOTOPHYSICS OF COORDINATION COMPOUNDS II, 2007, 281 :143-203
[10]   Visible-light-mediated radical oxydifluoromethylation of olefinic amides for the synthesis of CF2H-containing heterocycles [J].
Fu, Weijun ;
Han, Xin ;
Zhu, Mei ;
Xu, Chen ;
Wang, Zhiqiang ;
Ji, Baoming ;
Hao, Xin-Qi ;
Song, Mao-Ping .
CHEMICAL COMMUNICATIONS, 2016, 52 (91) :13413-13416
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