Photocatalytic reactions of fluoroalkyl iodides with alkenes

被引：9

作者：

Chernov, G. I. ^{[1
]}

Levin, V. V. ^{[2
]}

Dilman, A. D. ^{[2
]}

机构：

[1] Tomsk Polytech Univ, Res Sch Chem & Appl Biomed Sci, 30 prosp Lenina, Tomsk 634050, Russia

[2] Russian Acad Scienses, N D Zelinsky Inst Organ Chem, 47 Leninsky prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2023年 / 72卷 / 01期

关键词：

organofluorine chemistry; fluoroalkyl iodides; alkenes; photocatalysis; radicals; TRANSFER RADICAL-ADDITION; PHOTOREDOX CATALYSIS; PERFLUOROALKYL IODIDES; LIGHT; TRIFLUOROMETHYLATION; GENERATION; IODOPERFLUOROALKYLATION; ORGANOFLUORINE; COMPLEXES; ALKYNES;

D O I：

10.1007/s11172-023-3714-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluoroalkyl iodides are convenient sources of fluoroalkyl radicals under photocatalytic conditions. After the addition of a fluorine radical to a double bond, the resulting radical can react in several directions, including abstraction of an iodine atom from the starting iodide, abstraction of a hydrogen atom from a reducing agent, intramolecular interception by an aromatic system, and one-electron oxidation. These reactions make it possible to obtain a wide range of organofluorine compounds. The review summarizes data for the last five years.

引用

页码：61 / 72

页数：12

共 57 条

[41] (Fluoro)alkylation of alkenes promoted by photolysis of alkylzirconocenes [J].

Ren, Xiaoxiao ;

Gao, Xing ;

Min, Qiao-Qiao ;

Zhang, Shu ;

Zhang, Xingang .

CHEMICAL SCIENCE, 2022, 13 (12) :3454-3460

[42] Visible-Light-Mediated lodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate [J].

Rosso, Cristian ;

Williams, Jason D. ;

Filippini, Giacomo ;

Prato, Maurizio ;

Kappe, C. Oliver .

ORGANIC LETTERS, 2019, 21 (13) :5341-5345

[43] Highly Performing Iodoperfluoroalkylation of Alkenes Triggered by the Photochemical Activity of Perylene Diimides [J].

Rosso, Cristian ;

Filippini, Giacomo ;

Cozzi, Pier Giorgio ;

Gualandi, Andrea ;

Prato, Maurizio .

CHEMPHOTOCHEM, 2019, 3 (04) :193-197

[44] Solar Synthesis: Prospects in Visible Light Photocatalysis [J].

Schultz, Danielle M. ;

Yoon, Tehshik P. .

SCIENCE, 2014, 343 (6174) :985-+

[45] Photoredox Catalysis in Organic Chemistry [J].

Shaw, Megan H. ;

Twilton, Jack ;

MacMillan, David W. C. .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6898-6926

[46] Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow [J].

Straathof, Natan J. W. ;

Cramer, Sten E. ;

Hessel, Volker ;

Noel, Timothy .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (50) :15549-15553

[47] Visible light-mediated difluoroalkylation of electron-deficient alkenes [J].

Supranovich, Vyacheslav, I ;

Levin, Vitalij V. ;

Struchkova, Marina, I ;

Hu, Jinbo ;

Dilman, Alexander D. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :1637-1641

[48] Radical Silyldifluoromethylation of Electron-Deficient Alkenes [J].

Supranovich, Vyacheslav I. ;

Levin, Vitalij V. ;

Struchkova, Marina I. ;

Korlyukov, Alexander A. ;

Dilman, Alexander D. .

ORGANIC LETTERS, 2017, 19 (12) :3215-3218

[49] Visible-light-induced dearomative spirocyclization of N-benzylacrylamides toward perfluorinated azaspirocyclic cyclohexadienones [J].

Tang, Shi ;

Yuan, Li ;

Li, Zeng-Zeng ;

Peng, Zhi-Yuan ;

Deng, You-Lin ;

Wang, Liang-Neng ;

Huang, Gui-Xiu ;

Sheng, Rui-Long .

TETRAHEDRON LETTERS, 2017, 58 (22) :2127-2130

[50] Visible-light-induced perfluoroalkylationiarylmigration/desulfonylation cascades of conjugated tosyl amides [J].