Iron-catalyzed C-7 Selective NH 2 Amination of Indoles

7-Aminoindoles are important synthetic intermediates to a broad range of bioactive molecules. Transition metal-catalyzed directed C-H amination is among the most straightforward route for their synthesis, whereas methods that could directly incorporate an NH group in a highly selective manner remain...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 63; no. 45; p. e202412103
Main Authors Wang, Zhan-Lin, Cheng, Jin-Kai, Wang, Fei
Format Journal Article
LanguageEnglish
Published Germany 04.11.2024
Subjects
C−H functionalization
amination
site-selectivity
indole
iron catalysis
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Summary:7-Aminoindoles are important synthetic intermediates to a broad range of bioactive molecules. Transition metal-catalyzed directed C-H amination is among the most straightforward route for their synthesis, whereas methods that could directly incorporate an NH group in a highly selective manner remains elusive. Moreover, there is still high demand for the development of earth-abundant metal catalysis for such attractive reactivity. We present here the first C-7 selective NH amination of indoles through a directed homolytic aromatic substitution (HAS) with iron-aminyl radical. The reaction exhibits broad substrate scope, tolerates variety of functional groups, and is readily scalable with catalyst loading down to 0.1 mol % and turnover number (TON) up to 4500.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202412103