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Article: Iron porphyrin-catalysed C(sp3)–H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds

TitleIron porphyrin-catalysed C(sp3)–H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds
Authors
Issue Date7-Feb-2023
PublisherRoyal Society of Chemistry
Citation
Organic Chemistry Frontiers, 2023, v. 10, n. 6, p. 1368-1374 How to Cite?
Abstract

Transition metal-catalysed direct C–N bond formation via nitrenoid (metal–imido/nitrene complexes) insertion, such as C–H bond amination, is a powerful strategy for preparing nitrogen-containing organic compounds. In this context, metal catalysts based on iron are appealing due to iron's high Earth abundance and biocompatibility. Herein, we demonstrate that iron(III) NHC porphyrin-catalysed C(sp3)–H amination with alkyl azides, using [FeIII(TDCPP)(IMe)2]I (H2TDCPP = tetrakis(2,6-dichlorophenyl)porphyrin, IMe = 1,3-dimethylimidazol-2-ylidene) as a catalyst, offers a complementary approach for the synthesis of structurally complex organic compounds as exemplified by the synthesis of a panel of nitrogen-containing skeletons that are representative examples of various families of natural products and bioactive compounds.


Persistent Identifierhttp://hdl.handle.net/10722/331368
ISSN
2023 SCImago Journal Rankings: 1.016
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorFan, Jianqiang-
dc.contributor.authorWang, Ye-
dc.contributor.authorHu, Xuefu-
dc.contributor.authorLiu, Yungen-
dc.contributor.authorChe, Chi-Ming-
dc.date.accessioned2023-09-21T06:55:07Z-
dc.date.available2023-09-21T06:55:07Z-
dc.date.issued2023-02-07-
dc.identifier.citationOrganic Chemistry Frontiers, 2023, v. 10, n. 6, p. 1368-1374-
dc.identifier.issn2052-4110-
dc.identifier.urihttp://hdl.handle.net/10722/331368-
dc.description.abstract<p>Transition metal-catalysed direct C–N bond formation <em>via</em> nitrenoid (metal–imido/nitrene complexes) insertion, such as C–H bond amination, is a powerful strategy for preparing nitrogen-containing organic compounds. In this context, metal catalysts based on iron are appealing due to iron's high Earth abundance and biocompatibility. Herein, we demonstrate that iron(<small>III</small>) NHC porphyrin-catalysed C(sp<small><sup>3</sup></small>)–H amination with alkyl azides, using [Fe<small><sup>III</sup></small>(TDCPP)(IMe)<small><sub>2</sub></small>]I (H<small><sub>2</sub></small>TDCPP = tetrakis(2,6-dichlorophenyl)porphyrin, IMe = 1,3-dimethylimidazol-2-ylidene) as a catalyst, offers a complementary approach for the synthesis of structurally complex organic compounds as exemplified by the synthesis of a panel of nitrogen-containing skeletons that are representative examples of various families of natural products and bioactive compounds.<br></p>-
dc.languageeng-
dc.publisherRoyal Society of Chemistry-
dc.relation.ispartofOrganic Chemistry Frontiers-
dc.titleIron porphyrin-catalysed C(sp3)–H amination with alkyl azides for the synthesis of complex nitrogen-containing compounds-
dc.typeArticle-
dc.identifier.doi10.1039/d2qo01972h-
dc.identifier.scopuseid_2-s2.0-85148458805-
dc.identifier.volume10-
dc.identifier.issue6-
dc.identifier.spage1368-
dc.identifier.epage1374-
dc.identifier.eissn2052-4129-
dc.identifier.isiWOS:000928682700001-
dc.identifier.issnl2052-4110-

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