Iodine-Mediated α-C-H Amination of Carbonyl Compounds via Nitrogen-Directed Oxidative Umpolung
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Updated: Jul 26, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Manman Wang1, Xiaofei Yi1, Wenjun Ye1
1Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China.
Abstract:
A new synthetic strategy for direct C(sp3)-H amination of carbonyl compounds at their α-carbon has been established employing molecular iodine and nitrogen-directed oxidative umpolung. In this transformation, iodine acts not only as an iodinating reagent but also as a Lewis acid catalyst, and both the nitrogen-containing moiety and the carbonyl group in the substrate play important roles. This synthetic approach is applicable to a broad variety of carbonyl substrates, including esters, ketones, and amides. Its features also include no requirement for transition metals, mild reaction conditions, short reaction times, and gram-scale synthesis.
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