Interaction of gem-Difluorinated Iodides with Silyl Enol Ethers Mediated by Photoredox Catalysis

被引：30

作者：

Chernov, Grigory N. ^{[1
,2
]}

Levin, Vitalij V. ^{[1
]}

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

Struchkova, Marina I. ^{[1
]}

Dilman, Alexander D. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 17期

基金：

俄罗斯基础研究基金会;

关键词：

fluorine; photocatalysis; silyl enol ethers; radical reactions; fluoroalkylation; ALPHA-TRIFLUOROMETHYLATED KETONES; RADICAL TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; ORGANOZINC REAGENTS; UNACTIVATED OLEFINS; CARBONYL-COMPOUNDS; ROOM-TEMPERATURE; ALKENES; LIGHT;

D O I：

10.1002/adsc.201700423

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A method for the synthesis of beta, beta-difluorinated ketones by coupling of alpha, alpha-difluorinated iodides with silyl enol ethers is described. The reaction is performed in the presence of iridium(III) photocatalysts under the irradiation with 400 nm light emitting diodes.

引用

页码：3063 / 3067

页数：5

共 55 条

[1]

Al-Maharik N, 2011, ALDRICHIM ACTA, V44, P65

[2] OUTER-SPHERE DISSOCIATIVE ELECTRON-TRANSFER TO ORGANIC-MOLECULES - A SOURCE OF RADICALS OR CARBANIONS - DIRECT AND INDIRECT ELECTROCHEMISTRY OF PERFLUOROALKYL BROMIDES AND IODIDES [J].

ANDRIEUX, CP ;

GELIS, L ;

MEDEBIELLE, M ;

PINSON, J ;

SAVEANT, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3509-3520

[3] 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

[4] MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].

BLACKBURN, GM ;

ENGLAND, DA ;

KOLKMANN, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932

[5] Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones [J].

Deb, Arghya ;

Manna, Srimanta ;

Modak, Atanu ;

Patra, Tuhin ;

Maity, Soham ;

Maiti, Debabrata .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9747-9750

[6] Synthesis of organofluorine compounds using α-fluorine-substituted silicon reagents [J].

Dilman, Alexander D. ;

Levin, Vitalij V. .

MENDELEEV COMMUNICATIONS, 2015, 25 (04) :239-244

[7] Selective Incorporation of Difluoromethylene Moieties into Arenes Assisted by Transition Metals [J].

Gao, Bing ;

Ni, Chuanfa ;

Hu, Jinbo .

CHIMIA, 2014, 68 (06) :414-418

[8] Direct α-Siladifluoromethylation of Lithium Enolates with Ruppert-Prakash Reagent via C-F Bond Activation [J].

Hashimoto, Ryota ;

Iida, Toshiaki ;

Aikawa, Kohsuke ;

Ito, Shigekazu ;

Mikami, Koichi .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (10) :2750-2754

[9] Umpolung of Fluoroform by C?F Bond Activation: Direct Difluoromethylation of Lithium Enolates [J].

Iida, Toshiaki ;

Hashimoto, Ryota ;

Aikawa, Kohsuke ;

Ito, Shigekazu ;

Mikami, Koichi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) :9535-9538

[10] Radical trifluoromethylation of titanium ate enolate [J].

Itoh, Y ;

Mikami, K .

ORGANIC LETTERS, 2005, 7 (04) :649-651

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