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

来源：

CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 66期

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

页码：9453 / 9456

页数：4

共 59 条

[1] Radical Fluoroalkylation Reactions [J].

Barata-Vallejo, Sebastian ;

Victoria Cooke, Maria ;

Postigo, Al .

ACS CATALYSIS, 2018, 8 (08) :7287-7307

[2] COPPER-CATALYZED ADDITIONS OF ORGANIC POLYHALIDES TO OLEFINS - A VERSATILE SYNTHETIC TOOL [J].

BELLUS, D .

PURE AND APPLIED CHEMISTRY, 1985, 57 (12) :1827-1838

[3] Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade [J].

Buquoi, J. Quentin ;

Lear, Jeremy M. ;

Gu, Xin ;

Nagib, David A. .

ACS CATALYSIS, 2019, 9 (06) :5330-5335

[4] Heterocycle synthesis by copper facilitated addition of heteroatoms to alkenes, alkynes and arenes [J].

Chemler, Sherry R. ;

Fuller, Peter H. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1153-1160

[5] Interaction of gem-Difluorinated Iodides with Silyl Enol Ethers Mediated by Photoredox Catalysis [J].

Chernov, Grigory N. ;

Levin, Vitalij V. ;

Kokorekin, Vladimir A. ;

Struchkova, Marina I. ;

Dilman, Alexander D. .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) :3063-3067

[6]

Cismesia MA, 2015, CHEM SCI, V6, P5426, DOI 10.1039/c5sc02185e

[7] Recent Progress in Visible-Light Photoredox-Catalyzed Intermolecular 1,2-Difunctionalization of Double Bonds via an ATRA-Type Mechanism [J].

Courant, Thibaut ;

Masson, Geraldine .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6945-6952

[8] ADDITION OF FREE-RADICALS TO UNSATURATED SYSTEMS .23. PHOTOCHEMICAL AND THERMAL-REACTIONS OF TRIFLUOROIODOMETHANE WITH BUT-2-ENE AND BUT-1-ENE [J].

DAVIES, T ;

HASZELDINE, RN ;

TIPPING, AE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (04) :927-932

[9] Thiols, thioethers, and related compounds as sources of C-centred radicals [J].

Denes, Fabrice ;

Schiesser, Carl H. ;

Renaud, Philippe .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (19) :7900-7942

[10] Copper Catalyzed Atom Transfer Radical Addition (ATRA) and Cyclization (ATRC) Reactions in the Presence of Reducing Agents [J].

Eckenhoff, William T. ;

Pintauer, Tomislav .

CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2010, 52 (01) :1-59

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