Palladium-Catalyzed Oxidative Acetoxylation of Benzylic C–H Bond Using Bidentate Auxiliary

Pd(OAc)2-catalyzed oxidative acetoxylation of benzylic C–H bonds utilizing a bidentate system has been explored. A variety of picolinoyl- or quinoline-2-carbonyl-protected toluidine derivatives react with PhI(OAc)2 in the presence of Pd(OAc)2 to afford the acetoxylated products in synthetically usef...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-11, Vol.78 (21), p.10821-10831
Main Authors: Ju, Long, Yao, Jinzhong, Wu, Zaihong, Liu, Zhanxiang, Zhang, Yuhong
Format: Article
Language:English
Subjects:
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Benzyl Compounds - chemistry
Catalysis
Hydrogen Bonding
Oxidation-Reduction
Palladium - chemistry
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Summary:Pd(OAc)2-catalyzed oxidative acetoxylation of benzylic C–H bonds utilizing a bidentate system has been explored. A variety of picolinoyl- or quinoline-2-carbonyl-protected toluidine derivatives react with PhI(OAc)2 in the presence of Pd(OAc)2 to afford the acetoxylated products in synthetically useful yields. A broad of functionalities, such as CH3, F, Cl, Br, I, COCH3, CO2Et, SO2CH3, and NO2, were tolerated. This transformation provides easy access to 2-hydroxymethylaniline derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401830k