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Biomimetic Carbene‐Catalyzed Oxidations of Aldehydes Using TEMPO
Author(s) -
Guin Joyram,
De Sarkar Suman,
Grimme Stefan,
Studer Armido
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802735
Subject(s) - catalysis , chemistry , carbene , nitroxide mediated radical polymerization , hydrolysis , radical , organic chemistry , electron transfer , transition metal , combinatorial chemistry , photochemistry , radical polymerization , polymer , monomer
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.