Carboxyl group assisted isodesmic meta-C-H iodination of phenethylamines, benzylamines, and 2-aryl anilines

Isodesmic C-H activation reactions are still very limited and they represent mild alternatives to other C-H transformations that require reactive agents. Meanwhile, iodinating arenes at unconventional positions is challenging but also useful. Herein, we report a Pd-catalyzed remote isodesmic meta-C-H iodination of phenethylamines, benzylamines, and 2-aryl anilines using 1-iodo-4-methoxy-2-nitrobenzene as the mild iodinating reagent in a site-selective and chemo-selective manner. A range of valuable meta-iodinated and even multi-halogenated amines were afforded smoothly, paving the way for synthetic chemists to access various amine derivatives at the challenging meta-positions.

Automated summary

This study reports a Pd-catalyzed remote isodesmic meta-C-H iodination of phenethylamines, benzylamines, and 2-aryl anilines using 1-iodo-4-methoxy-2-nitrobenzene as the mild iodinating reagent. A range of valuable meta-iodinated and even multi-halogenated amines were successfully synthesized, paving the way for synthetic chemists to access various amine derivatives at the challenging meta-positions.