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Article: Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides
Title | Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides |
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Authors | |
Keywords | Attractive strategies Bioactive compounds C-n bond formations Insertion reactions Mechanistic studies |
Issue Date | 2020 |
Publisher | Royal Society of Chemistry: Open Access. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.asp |
Citation | Chemical Science, 2020, v. 11 n. 18, p. 4680-4686 How to Cite? |
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. |
Persistent Identifier | http://hdl.handle.net/10722/290121 |
ISSN | 2023 Impact Factor: 7.6 2023 SCImago Journal Rankings: 2.333 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Du, YD | - |
dc.contributor.author | Zhou, CY | - |
dc.contributor.author | To, WP | - |
dc.contributor.author | Wang, HX | - |
dc.contributor.author | Che, CM | - |
dc.date.accessioned | 2020-10-22T08:22:23Z | - |
dc.date.available | 2020-10-22T08:22:23Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Chemical Science, 2020, v. 11 n. 18, p. 4680-4686 | - |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.uri | http://hdl.handle.net/10722/290121 | - |
dc.description.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. | - |
dc.language | eng | - |
dc.publisher | Royal Society of Chemistry: Open Access. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.asp | - |
dc.relation.ispartof | Chemical Science | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject | Attractive strategies | - |
dc.subject | Bioactive compounds | - |
dc.subject | C-n bond formations | - |
dc.subject | Insertion reactions | - |
dc.subject | Mechanistic studies | - |
dc.title | Iron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides | - |
dc.type | Article | - |
dc.identifier.email | Zhou, CY: cyzhou@hku.hk | - |
dc.identifier.email | To, WP: kevintwp@hku.hk | - |
dc.identifier.email | Wang, HX: wanghx1@hku.hk | - |
dc.identifier.email | Che, CM: chemhead@hku.hk | - |
dc.identifier.authority | Zhou, CY=rp00843 | - |
dc.identifier.authority | To, WP=rp02410 | - |
dc.identifier.authority | Che, CM=rp00670 | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.1039/D0SC00784F | - |
dc.identifier.scopus | eid_2-s2.0-85086046432 | - |
dc.identifier.hkuros | 315950 | - |
dc.identifier.volume | 11 | - |
dc.identifier.issue | 18 | - |
dc.identifier.spage | 4680 | - |
dc.identifier.epage | 4686 | - |
dc.identifier.isi | WOS:000535674600008 | - |
dc.publisher.place | United Kingdom | - |
dc.identifier.issnl | 2041-6520 | - |