Direct Synthesis of Unprotected Indolines Through Intramolecular sp3 C-H Amination Using Nitroarenes as Aryl Nitrene Precursors
Given the prevalence of molecules containing nitro groups in organic synthesis, innovative methods to expand the reactivity of this functional group are of interest in both industrial and academic settings. In this report, a metal-free intramolecular benzylic sp3 C-H amination is disclosed using ary...
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| Veröffentlicht in: | Chemistry : a European journal 2023-09, Vol.29 (54), p.e202301978-e202301978 |
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| container_end_page | e202301978 |
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| container_issue | 54 |
| container_start_page | e202301978 |
| container_title | Chemistry : a European journal |
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| creator | Sirvinskaite, Giedre Nardo, Celine S Müller, Patrick Gasser, Aurelio C Morandi, Bill |
| description | Given the prevalence of molecules containing nitro groups in organic synthesis, innovative methods to expand the reactivity of this functional group are of interest in both industrial and academic settings. In this report, a metal-free intramolecular benzylic sp3 C-H amination is disclosed using aryl nitro compounds as aryl nitrene precursors. Organosilicon reagent N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene (Si-DHBP) served as an efficient reductant in the transformation, enabling the in situ generation of aryl nitrene species for the direct, metal-free synthesis of unprotected 2-arylindolines from the corresponding nitroarene compounds. |
| doi_str_mv | 10.1002/chem.202301978 |
| format | Article |
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In this report, a metal-free intramolecular benzylic sp3 C-H amination is disclosed using aryl nitro compounds as aryl nitrene precursors. Organosilicon reagent N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene (Si-DHBP) served as an efficient reductant in the transformation, enabling the in situ generation of aryl nitrene species for the direct, metal-free synthesis of unprotected 2-arylindolines from the corresponding nitroarene compounds.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202301978</identifier><identifier>PMID: 37404217</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Amination ; Aromatic compounds ; Chemical synthesis ; Chemistry ; Functional groups ; Heterocyclic compounds ; Nitro compounds ; Precursors ; Reagents ; Reducing agents</subject><ispartof>Chemistry : a European journal, 2023-09, Vol.29 (54), p.e202301978-e202301978</ispartof><rights>2023 Wiley-VCH GmbH.</rights><rights>2023. 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| source | Wiley Online Library All Journals |
| subjects | Amination Aromatic compounds Chemical synthesis Chemistry Functional groups Heterocyclic compounds Nitro compounds Precursors Reagents Reducing agents |
| title | Direct Synthesis of Unprotected Indolines Through Intramolecular sp3 C-H Amination Using Nitroarenes as Aryl Nitrene Precursors |
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