Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO

被引：330

作者：

Guin, Joyram ^{[1
]}

De Sarkar, Suman ^{[1
]}

Grimme, Stefan ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, NRW Grad Sch Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 45期

关键词：

carbenes; density functional calculations; organocatalysis; oxidations; synthetic methods;

D O I：

10.1002/anie.200802735

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Transition-metal-free organocatalytic oxidations of various aldehydes proceed with the TEMPO radical as a mild organic oxidant; the resulting TEMPO esters are formed in moderate to excellent yields (see scheme). N-Heterocyclic carbenes (NHCs) are efficient catalysts and activate aldehydes for electron-transfer reactions. The TEMPO esters are readily hydrolyzed and the nitroxide can be regenerated by aerobic oxidation. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8727 / 8730

页数：4

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