Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides

Abstract

Visible light driven nitrene transfer and insertion reactions of organic azides are an attractive strategy for the design of C-N bond formation reactions under mild reaction conditions, the challenge being lack of selectivity as a free nitrene reactive intermediate is usually involved. Herein is described an iron(iii) porphyrin catalysed sp³ C-H amination and alkene aziridination with selectivity by using organic azides as the nitrogen source under blue LED light (469 nm) irradiation. The photochemical reactions display chemo- and regio-selectivity and are effective for the late-stage functionalization of natural and bioactive compounds with complexity. Mechanistic studies revealed that iron porphyrin plays a dual role as a photosensitizer and as a catalyst giving rise to a reactive iron-nitrene intermediate for subsequent C-N bond formation.