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Updated: Aug 8, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Iron Catalysis of C(sp3)-H Azidation Using a Heteroarene Radical Cation Strategy
A Young Ji1, Annaram Thirupathi1, Joon Young Hwang1
1Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea.
Abstract:
The FeIII(phen)3 catalysis of the benzylic C(sp3)-H azidation of indoles has been investigated. The Fe(III) complex can selectively oxidize indoles to form arene radical cations, which are transformed into benzylic C(sp3) radical intermediates. This strategy exhibits a difference in reactivity between N-heteroarenes and benzene, which is difficult to achieve via direct hydrogen abstraction approaches. Various biorelevant azide precursors were constructed, highlighting the utility of this mild first-row transition-metal catalyst system.
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