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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...

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Autores principales: Noda, Hidetoshi, Asada, Yasuko, Shibasaki, Masakatsu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2023
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.
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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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