Methodology development for the direct and selective amination of C–H bonds in which selectivity relies only on catalyst control has been a longstanding challenge in modern organic synthesis. Previously, tunable and chemoselective nitrene transfer in carbamates was achieved by altering the metal-to-ligand ratio in a silver-catalyzed system to selectively yield either aziridines or C–H insertion products. This idea of tunable reactivity has been extended to intramolecular site-selective C–H aminations of sulfamates in which silver catalysts supported by common nitrogenated ligands are used. In these reactions, judicious ligand choice results in the ability to tune a nitrene transfer reaction for the amination of two chemically distinct C–H bonds.

Ligand-controlled, tunable silver-catalyzed C–H amination

249th National Meeting (2015)

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