Photocatalytic α-Oxyamination of Stable Enolates, Silyl Enol Ethers, and 2-Oxoalkane Phosphonic Esters

被引：35

作者：

Schroll, Peter ^{[1
]}

Koenig, Burkhard ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 02期

关键词：

Photooxidation; Photocatalysis; Radicals; Flow catalysis; Microreactors; LIGHT-DRIVEN OXIDATION; VISIBLE-LIGHT; AEROBIC OXIDATION; 1,3-DICARBONYL COMPOUNDS; PHOTOREDOX CATALYSIS; ALCOHOLS; ALDEHYDES; EFFICIENT; RADICALS; ALKENES;

D O I：

10.1002/ejoc.201403433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fast alpha-oxyamination of stable enolates, silyl enol ethers, and in situ deprotonated dialkyl 2-oxoalkane phosphonates and diphenyl-2-oxoalkyl phosphine oxides was performed in the presence of [Ru(bpy)(3)](2+) (bpy = 2,2'-bipyridyl) as a photocatalyst, 2,2,6,6-tetramethylpiperidine nitroxide (TEMPO), and visible light. The key step was the light-induced one-electron oxidation of TEMPO into the 2,2,6,6-tetramethylpiperidine1- oxoammonium ion, which was nucleophilically attacked to yield alpha-functionalized carbonyl compounds. The reaction time was significantly reduced by the use of the microreactor flow technique.

引用

页码：309 / 313

页数：5

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