Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO

Biomimetic Carbene-Catalyzed Oxidations of Aldehydes Using TEMPO

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 electr...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-10, Vol.47 (45), p.8727-8730
Hauptverfasser: Guin, Joyram, De Sarkar, Suman, Grimme, Stefan, Studer, Armido
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Biomimetics
carbenes
Catalysis
Cyclic N-Oxides - chemistry
density functional calculations
Esters - chemical synthesis
Esters - chemistry
Heterocyclic Compounds - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
organocatalysis
Oxidation-Reduction
oxidations
Stereoisomerism
synthetic methods
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200802735