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

A palladium-catalyzedolefination of meta-C-Hbonds in arenes containing oxyamides using a nitrile template as thedirecting group has been established. The methodology exhibited high meta-selectivity and tolerated different functional groupssuch as benzyloxyamides and olefin substrates. The desired productswere obtained in good yields. This approach enabled the modificationof natural products and drugs and was also applicable on the gram-scale.Furthermore, the directing template was readily removed by selectivecleavage 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 noveldrugs.

Automated summary

A palladium-catalyzed olefination of meta-C-H bonds in arenes containing oxyamides using a nitrile template as the directing group has been developed. This method exhibited high meta-selectivity and demonstrated compatibility with various functional groups such as benzyloxyamides and olefins. The desired products were obtained in good yields. The approach allowed for the modification of natural products and drugs and was also scalable. Additionally, the directing template could be easily removed to obtain meta-functionalized hydroxylamines and benzyl alcohols by selective cleavage of the amide bond or the O-N bond. This method holds great potential for the design of novel drugs.