Iodine-Mediated α-C-H Amination of Carbonyl Compounds via Nitrogen-Directed Oxidative Umpolung

A new synthetic strategy for direct C(sp (3))-H amination of carbonyl compounds at their alpha-carbonhas been established employing molecular iodine and nitrogen-directedoxidative umpolung. In this transformation, iodine acts not only asan iodinating reagent but also as a Lewis acid catalyst, and boththe nitrogen-containing moiety and the carbonyl group in the substrateplay important roles. This synthetic approach is applicable to a broadvariety of carbonyl substrates, including esters, ketones, and amides.Its features also include no requirement for transition metals, mildreaction conditions, short reaction times, and gram-scale synthesis.

Automated summary

A new synthetic strategy for direct C(sp(3))-H amination of carbonyl compounds has been established using molecular iodine and nitrogen-directed oxidative umpolung. This approach is applicable to various carbonyl substrates, does not require transition metals, has mild reaction conditions, short reaction times, and can be used for gram-scale synthesis.