3 years ago

Trans-selective γ-arylation of macrocyclic N-picolinoylcycloalkylamines through palladium-catalyzed methylene sp3 carbon–hydrogen bond activation

Trans-selective γ-arylation of macrocyclic N-picolinoylcycloalkylamines through palladium-catalyzed methylene sp3 carbon–hydrogen bond activation
While numerous stereoselective methylene β- and γ-carbon–hydrogen activation reactions are reported, there are no examples of trans-selective γ-carbon–hydrogen activation of cyclic compounds. Herein I report the first trans-selective palladium-catalyzed γ-arylation of N-picolinoylcycloalkylamine with aryl iodides. Trans-arylation of macrocyclic N-picolinoylcyclododecylamine proceeded to give trans-3-aryl-N-picolinoylcyclododecylamine as a sole mono-arylated product in up to 85% yield. Other, larger substrates were also applicable to trans-arylation, albeit with lower efficiency. The picolinoyl group of the trans-arylated product was easily removed with zinc and diluted hydrochloric acid.

Publisher URL: www.sciencedirect.com/science

DOI: S0040403917311826

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