Palladium(II)-Catalyzed Remote meta-C–H Functionalization of Arenes Enabled by Multitasking Oxyamides as the Linker

A palladium-catalyzed olefination of meta-C–H bonds in arenes containing oxyamides using a nitrile template as the directing group has been established. The methodology exhibited high meta-selectivity and tolerated different functional groups such as benzyloxyamides and olefin substrates. The desire...

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Bibliographic Details
Published in:Organic letters 2023-06, Vol.25 (24), p.4416-4421
Main Authors: Zhu, Yue-Lu, Sun, Qiu-Xue, Feng, Jin-Shuo, Shao, You-Dong, Chen, Jiao
Format: Article
Language:English
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Summary:A palladium-catalyzed olefination of meta-C–H bonds in arenes containing oxyamides using a nitrile template as the directing group has been established. The methodology exhibited high meta-selectivity and tolerated different functional groups such as benzyloxyamides and olefin substrates. The desired products were obtained in good yields. This approach enabled the modification of natural products and drugs and was also applicable on the gram-scale. Furthermore, the directing template was readily removed by selective cleavage of the amide bond or the O–N bond to obtain meta-functionalized hydroxylamines and benzyl alcohols. The proposed method holds great potential for the design of novel drugs.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01101