Copper-Catalyzed Aerobic Aliphatic C–H Oxygenation Directed by an Amidine Moiety

A method for the oxygenation of tertiary C–H bonds of N-alkylamidines and N-(2-alkylaryl)amidines is described that utilizes the CuBr·SMe2/2,2′-bipyridine catalytic system under an O2 atmosphere and provides dihydrooxazoles and 4H-1,3-benzoxazines. The oxygen atom is incorporated from atmospheric mo...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 29; pp. 11980 - 11983
Main Authors Wang, Yi-Feng, Chen, Hui, Zhu, Xu, Chiba, Shunsuke
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.07.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OXIDATION REACTIONS
COMPLEX
REAGENTS
FUNCTIONALIZATIONS
BONDS
HYDROXYLATION
OXIDANT
OLEFINS
DERIVATIVES
INSIGHTS
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Summary:A method for the oxygenation of tertiary C–H bonds of N-alkylamidines and N-(2-alkylaryl)amidines is described that utilizes the CuBr·SMe2/2,2′-bipyridine catalytic system under an O2 atmosphere and provides dihydrooxazoles and 4H-1,3-benzoxazines. The oxygen atom is incorporated from atmospheric molecular oxygen during the present process.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja305833a