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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Synthesis of medium-sized heterocycles from oxetanes based on an allylic amination/ring-opening strategy
Jixing Li1, Ming Fang1, Maoyan Liao1
1Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China. huanghai@cczu.edu.cn.
Abstract:
The construction of medium-sized ring compounds has been a prominent research area in synthetic chemistry. In this study, we developed a tandem strategy that combines allylic amination and ring-opening of oxetanes to synthesize medium-sized heterocycles. Specifically, N-aryl oxetan-3-amines undergo allylic amination with zwitterionic π-allylpalladium, followed by intramolecular ring-opening, resulting in the formation of medium-sized heterocycles. Notably, we are able to achieve the synthesis of 7-8 membered heterocycles with moderate to good yields by employing different types of zwitterionic π-allylpalladium species.
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