Iron Catalysis of C(sp<sup>3</sup>)–H Azidation Using a Heteroarene Radical Cation Strategy
Ao Ji, Annaram Thirupathi, Joon Young Hwang, Yuri Kim, Gyuri Han, Kwang‐Hyun Ahn, Kyungtae Kang, Eun Joo Kang
Abstract
The Fe III (phen) 3 catalysis of the benzylic C(sp 3 )–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(sp 3 ) 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.
Topics & Concepts
ChemistryCatalysisCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsOxidative Organic Chemistry Reactions