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Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines
In this study, the reactivity of the alkyl nitrenes, generated from the substituted hydroxylamine precursors, was determined using the same rhodium catalyst. The results revealed that in competitive C–H insertion experiments, the regioselectivity between benzylic and tertiary C–H bonds could be modu...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10654751/ https://www.ncbi.nlm.nih.gov/pubmed/38025067 http://dx.doi.org/10.3389/fchem.2023.1271896 |
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author | Noda, Hidetoshi Asada, Yasuko Shibasaki, Masakatsu |
author_facet | Noda, Hidetoshi Asada, Yasuko Shibasaki, Masakatsu |
author_sort | Noda, Hidetoshi |
collection | PubMed |
description | In this study, the reactivity of the alkyl nitrenes, generated from the substituted hydroxylamine precursors, was determined using the same rhodium catalyst. The results revealed that in competitive C–H insertion experiments, the regioselectivity between benzylic and tertiary C–H bonds could be modulated by adding Brønsted acids or changing the substituents on oxygen. This study enhances our understanding of the metallonitrene structures and provides valuable insights for further development of selective N-heterocycle syntheses. |
format | Online Article Text |
id | pubmed-10654751 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-106547512023-01-01 Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines Noda, Hidetoshi Asada, Yasuko Shibasaki, Masakatsu Front Chem Chemistry In this study, the reactivity of the alkyl nitrenes, generated from the substituted hydroxylamine precursors, was determined using the same rhodium catalyst. The results revealed that in competitive C–H insertion experiments, the regioselectivity between benzylic and tertiary C–H bonds could be modulated by adding Brønsted acids or changing the substituents on oxygen. This study enhances our understanding of the metallonitrene structures and provides valuable insights for further development of selective N-heterocycle syntheses. Frontiers Media S.A. 2023-11-03 /pmc/articles/PMC10654751/ /pubmed/38025067 http://dx.doi.org/10.3389/fchem.2023.1271896 Text en Copyright © 2023 Noda, Asada and Shibasaki. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Noda, Hidetoshi Asada, Yasuko Shibasaki, Masakatsu Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
title | Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
title_full | Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
title_fullStr | Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
title_full_unstemmed | Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
title_short | Examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
title_sort | examining the effects of additives and precursors on the reactivity of rhodium alkyl nitrenes generated from substituted hydroxylamines |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10654751/ https://www.ncbi.nlm.nih.gov/pubmed/38025067 http://dx.doi.org/10.3389/fchem.2023.1271896 |
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