American Chemical Society
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Iron Catalysis of C(sp3)–H Azidation Using a Heteroarene Radical Cation Strategy

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journal contribution
posted on 2023-03-01, 15:34 authored by A. Young Ji, Annaram Thirupathi, Joon Young Hwang, Yuri Kim, Gyuri Han, Kwang-Hyun Ahn, Kyungtae Kang, Eun Joo Kang
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.