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
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
收藏
页码:309 / 313
页数:5
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