Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

被引：31

作者：

Scherbinina, Sofya I. ^{[1
,2
]}

Fedorov, Oleg V. ^{[1
]}

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 24期

基金：

俄罗斯科学基金会;

关键词：

FLUOROALKYLATION REACTIONS; ALPHA-FLUOROALKYLATION; METAL-COMPLEXES; LIGHT; FLUORINATION; CATALYSIS; PYRIDINES; ARYL; DIFLUOROHOMOLOGATION; DEOXYFLUORINATION;

D O I：

10.1021/acs.joc.7b02467

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of alpha,alpha-difluoro-beta-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)(3) under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that alpha,alpha-dilluoro-beta-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.

引用

页码：12967 / 12974

页数：8

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