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Pd‐Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation
Author(s) -
Giri Ramesh,
Liang Jue,
Lei JianGuang,
Li JiaoJie,
Wang DongHui,
Chen Xiao,
Naggar Isaac Clement,
Guo Chengyun,
Foxman Bruce M.,
Yu JinQuan
Publication year - 2005
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.200502767
Subject(s) - stereoselectivity , catalysis , chemistry , dual role , dual (grammatical number) , medicinal chemistry , organic chemistry , combinatorial chemistry , art , literature
Unactivated CH 3 groups in 2‐oxazolines are oxidized by inexpensive oxidants, such as tert‐ butyl peroxyacetate and lauroyl peroxide, in the presence of a catalytic amount of Pd(OAc) 2 . Carboxylic anhydrides are essential for both the oxidation of the PdC bonds and regeneration of Pd(OAc) 2 . The use of [D 6 ]Ac 2 O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).