Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

被引：1

作者：

Supranovich, Vyacheslav, I ^{[1
]}

Dmitriev, Igor A. ^{[1
,2
]}

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, Ninskie Gory 1-3, Moscow 119991, Russia

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 16卷

基金：

俄罗斯基础研究基金会;

关键词：

difluoroalkylation; nitrones; organofluorine compounds; photocatalysis; radical addition; US FDA; FLUORINE; DEOXYFLUORINATION; HETEROCYCLES; CHEMISTRY;

D O I：

10.3762/bjoc.16.260

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N-O bond.

引用

页码：3104 / 3108

页数：5

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