A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes

被引：82

作者：

Zubkov, Mikhail O. ^{[1
,2
]}

Kosobokov, Mikhail D. ^{[1
]}

Levin, Vitalij V. ^{[1
]}

Kokorekin, Vladimir A. ^{[1
,3
]}

Korlyukov, Alexander A. ^{[4
,5
]}

Hu, Jinbo ^{[6
]}

Dilman, Alexander D. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] D Mendeleev Univ Chem Technol Russia, Higher Chem Coll, 9 Miusskaya Sq, Moscow 125047, Russia

[3] IM Sechenov First Moscow State Med Univ, 8-2 Trubetskaya St, Moscow 119991, Russia

[4] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28 Vavilova St, Moscow 119991, Russia

[5] Pirogov Russian Natl Res Med Univ, 1 Ostrovitianov St, Moscow 117997, Russia

[6] Univ Chinese Acad Sci, Chinese Acad Sci, Key Lab Organofluorine Chem, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China

来源：

CHEMICAL SCIENCE | 2020年 / 11卷 / 03期

基金：

俄罗斯基础研究基金会;

关键词：

TRIFLUOROMETHYLATION; CATALYSIS; FLUOROALKYLATION; REAGENTS; ACCESS;

D O I：

10.1039/c9sc04643g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A 4-tetrafluoropyridinylthio group was suggested as a new photoredox-active moiety. The group can be directly installed on difluorostyrenes in a single step by the thiolene click reaction. It proceeds upon visible light catalysis with 9-phenylacridine providing various difluorinated sulfides as radical precursors. Single electron reduction of the C-S bond with the formation of fluoroalkyl radicals is enabled by the electron-poor azine ring. The intermediate difluorinated sulfides were involved in a series of photoredox reactions with silyl enol ethers, alkenes, nitrones and an alkenyl trifluoroborate.

引用

页码：737 / 741

页数：5

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