Iron Corrole-Catalyzed Intramolecular Amination Reactions of Alkyl Azides. Spectroscopic Characterization and Reactivity of [Fe^V(Cor)(NAd)].

ABSTRACT: As nitrogen analogues of iron-oxo species, high-valent iron-imido species have attracted great interest in the past decades. Fe^V-alkylimido species are generally considered to be key reaction intermediates in Fe(III)-catalyzed C(sp³)─H bond aminations of alkyl azides but remain underexplored. Here, it is reported that iron-corrole (Cor) complexes can catalyze a wide range of intramolecular C─H amination reactions of alkyl azides to afford a variety of 5-, 6- and 7-membered N-heterocycles, including alkaloids and natural product derivatives, with up to 3880 turnover numbers (TONs) and excellent diastereoselectivity (>99:1 d.r.). Mechanistic studies including density functional theory (DFT) calculations and intermolecular hydrogen atom abstraction (HAA) reactions reveal

SUBMITTER: You T 

PROVIDER: S-EPMC11497103 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature