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

Organic Chemistry Frontiers Pub Date: 2023-06-14 DOI: 10.1039/D3QO00479A

Abstract

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.

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