Fluoroalkyl sulfides as photoredox-active coupling reagents for alkene difunctionalization

被引:42
作者
Kosobokov, Mikhail D. [1 ]
Zubkov, Mikhail O. [1 ]
Levin, Vitalij V. [1 ]
Kokorekin, Vladimir A. [1 ]
Dilman, Alexander D. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
TRANSFER RADICAL-ADDITION; LIGHT; CYANOFLUOROALKYLATION; CYCLIZATION; FLUORINE; OLEFINS; SYSTEMS; ATRA;
D O I
10.1039/d0cc04617e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A visible-light-promoted fluoroalkylation-thiolation of alkenes is described. A 4-tetrafluoropyridinylthio fragment serves as a photoredox-active group in the initiation step and undergoes a radical group transfer, which is important for the reaction efficiency. In the primary products, the pyridinylthio substituent may be further functionalizedviaradical processes or an aromatic substitution reaction.
引用
收藏
页码:9453 / 9456
页数:4
相关论文
共 59 条
[21]   Recent Advances in Radical Difunctionalization of Simple Alkenes [J].
Lan, Xing-Wang ;
Wang, Nai-Xing ;
Xing, Yalan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (39) :5821-5851
[22]   Progress in Difluoroalkylation of Organic Substrates by Visible Light Photoredox Catalysis [J].
Lemos, Agostinho ;
Lemaire, Christian ;
Luxen, Andre .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) :1500-1537
[23]   Difunctionalization of Alkenes Involving Metal Migration [J].
Li, Yuqiang ;
Wu, Dong ;
Cheng, Hong-Gang ;
Yin, Guoyin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (21) :7990-8003
[24]   Visible-Light-Induced Hydrodifluoromethylation of Alkenes with a Bromodifluoromethylphosphonium Bromide [J].
Lin, Qing-Yu ;
Xu, Xiu-Hua ;
Zhang, Ke ;
Qing, Feng-Ling .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) :1479-1483
[25]   Atom Transfer Radical Reactions as a Tool for Olefin Functionalization - On the Way to Practical Applications [J].
Maria Munoz-Molina, Jose ;
Belderrain, Tomas R. ;
Perez, Pedro J. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (21) :3155-3164
[26]   Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design [J].
Meanwell, Nicholas A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (14) :5822-5880
[27]   Light on Unsaturated Hydrocarbons - "Gotta Heterofunctionalize Them All" [J].
Menigaux, Doriane ;
Belmont, Philippe ;
Brachet, Etienne .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) :2008-2055
[28]   Addition of CF3 across unsaturated moieties: a powerful functionalization tool [J].
Merino, Estibaliz ;
Nevado, Cristina .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (18) :6598-6608
[29]   Fluorine in pharmaceuticals:: Looking beyond intuition [J].
Mueller, Klaus ;
Faeh, Christoph ;
Diederich, Francois .
SCIENCE, 2007, 317 (5846) :1881-1886
[30]   Photoredox mediated annelation of iododifluoromethylated alcohols with 1,1-diarylethylenes [J].
Panferova, Liubov I. ;
Chernov, Grigory N. ;
Levin, Vitalij V. ;
Kokorekin, Vladimir A. ;
Dilman, Alexander D. .
TETRAHEDRON, 2018, 74 (50) :7136-7142