Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides |
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| Authors: | Yi-Dan Du Cong-Ying Zhou Wai-Pong To Hai-Xu Wang Chi-Ming Che |
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| Institution: | State Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, China.; HKU Shenzhen Institute of Research & Innovation, Shenzhen China ; Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai China |
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| 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.An iron(iii) porphyrin catalysed sp3 C–H amination and alkene aziridination with broad substrate scope under mild conditions is conducted, with selectivity through the use of organic azides as the nitrogen source under blue LED light irradiation. |
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