Efficient Benzylic and Aliphatic C–H Oxidation with Selectivity for Methylenic Sites Catalyzed by a Bioinspired Manganese Complex

A benzimidazole-based nonheme manganese complex efficiently catalyzes benzylic, aliphatic C–H as well as tertiary C–H oxidation with hydrogen peroxide as the oxidant in the presence of acetic acid as additive. 18O labeling experiments suggest the reaction may proceed via a high-valent manganese-oxo...

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Bibliographic Details
Published in:Organic letters 2014-02, Vol.16 (4), p.1108-1111
Main Authors: Shen, Duyi, Miao, Chengxia, Wang, Shoufeng, Xia, Chungu, Sun, Wei
Format: Article
Language:English
Subjects:
Benzimidazoles - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrogen Peroxide - chemistry
Magnetic Resonance Spectroscopy
Manganese - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Oxidation-Reduction
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Summary:A benzimidazole-based nonheme manganese complex efficiently catalyzes benzylic, aliphatic C–H as well as tertiary C–H oxidation with hydrogen peroxide as the oxidant in the presence of acetic acid as additive. 18O labeling experiments suggest the reaction may proceed via a high-valent manganese-oxo intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4037083