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

TitleIron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides
Authors
KeywordsAttractive strategies
Bioactive compounds
C-n bond formations
Insertion reactions
Mechanistic studies
Issue Date2020
PublisherRoyal 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?
AbstractVisible 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 Identifierhttp://hdl.handle.net/10722/290121
ISSN
2019 Impact Factor: 9.346
2015 SCImago Journal Rankings: 4.974
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorDu, YD-
dc.contributor.authorZhou, CY-
dc.contributor.authorTo, WP-
dc.contributor.authorWang, HX-
dc.contributor.authorChe, CM-
dc.date.accessioned2020-10-22T08:22:23Z-
dc.date.available2020-10-22T08:22:23Z-
dc.date.issued2020-
dc.identifier.citationChemical Science, 2020, v. 11 n. 18, p. 4680-4686-
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10722/290121-
dc.description.abstractVisible 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.languageeng-
dc.publisherRoyal Society of Chemistry: Open Access. The Journal's web site is located at http://www.rsc.org/publishing/journals/sc/About.asp-
dc.relation.ispartofChemical Science-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.subjectAttractive strategies-
dc.subjectBioactive compounds-
dc.subjectC-n bond formations-
dc.subjectInsertion reactions-
dc.subjectMechanistic studies-
dc.titleIron porphyrin catalysed light driven C–H bond amination and alkene aziridination with organic azides-
dc.typeArticle-
dc.identifier.emailZhou, CY: cyzhou@hku.hk-
dc.identifier.emailTo, WP: kevintwp@hku.hk-
dc.identifier.emailWang, HX: wanghx1@hku.hk-
dc.identifier.emailChe, CM: chemhead@hku.hk-
dc.identifier.authorityZhou, CY=rp00843-
dc.identifier.authorityTo, WP=rp02410-
dc.identifier.authorityChe, CM=rp00670-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1039/D0SC00784F-
dc.identifier.scopuseid_2-s2.0-85086046432-
dc.identifier.hkuros315950-
dc.identifier.volume11-
dc.identifier.issue18-
dc.identifier.spage4680-
dc.identifier.epage4686-
dc.identifier.isiWOS:000535674600008-
dc.publisher.placeUnited Kingdom-
dc.identifier.issnl2041-6520-

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