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Updated: Jun 11, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Manganese-Catalyzed Cycloalkene Ring Expansion Synthesis of Azaheterocycles
Zhixin Wang1, Hanxiao Xu1, Xuanzhen Han1
1Department of Polymer Science and Engineering, School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, China.
Abstract:
Herein, a Mn catalytic protocol has been developed for the cycloalkene ring expansion synthesis of azaheterocycles, allowing broad-substrate-scope access to pyridine and isoquinoline derivatives. The initial monoaddition of an azidyl radical to alkene and further as-generated C-radical addition to O2, followed by intramolecular rearrangement and aromatization, showcase a distinct Mn-catalyzed radical reactivity mode. The reaction features a short reaction time and a broad substrate scope, with applications demonstrated in complex structure elaboration and gram-scale vismodegib synthesis.
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