Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides

An efficient method to prepare organomagnesium intermediates having a protected azido group is reported. Protection of azido groups with di-(tert-butyl)(4-(dimethylamino)phenylphosphine (amphos) and following iodine–magnesium exchange realized the preparation of organomagnesium intermediates, which...

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Autores principales: Namioka, Rina, Suzuki, Minori, Yoshida, Suguru
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10424848/
https://www.ncbi.nlm.nih.gov/pubmed/37583567
http://dx.doi.org/10.3389/fchem.2023.1237878
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author Namioka, Rina
Suzuki, Minori
Yoshida, Suguru
author_facet Namioka, Rina
Suzuki, Minori
Yoshida, Suguru
author_sort Namioka, Rina
collection PubMed
description An efficient method to prepare organomagnesium intermediates having a protected azido group is reported. Protection of azido groups with di-(tert-butyl)(4-(dimethylamino)phenylphosphine (amphos) and following iodine–magnesium exchange realized the preparation of organomagnesium intermediates, which served in the synthesis of diverse azides by transformation with various electrophiles followed by deprotection with elemental sulfur. Furthermore, click reactions of azides with alkynes enabled synthesizing a wide variety of 1,2,3-triazoles.
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spelling pubmed-104248482023-08-15 Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides Namioka, Rina Suzuki, Minori Yoshida, Suguru Front Chem Chemistry An efficient method to prepare organomagnesium intermediates having a protected azido group is reported. Protection of azido groups with di-(tert-butyl)(4-(dimethylamino)phenylphosphine (amphos) and following iodine–magnesium exchange realized the preparation of organomagnesium intermediates, which served in the synthesis of diverse azides by transformation with various electrophiles followed by deprotection with elemental sulfur. Furthermore, click reactions of azides with alkynes enabled synthesizing a wide variety of 1,2,3-triazoles. Frontiers Media S.A. 2023-07-31 /pmc/articles/PMC10424848/ /pubmed/37583567 http://dx.doi.org/10.3389/fchem.2023.1237878 Text en Copyright © 2023 Namioka, Suzuki and Yoshida. 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
Namioka, Rina
Suzuki, Minori
Yoshida, Suguru
Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides
title Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides
title_full Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides
title_fullStr Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides
title_full_unstemmed Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides
title_short Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides
title_sort synthesis of 1,2,3-triazoles using grignard reactions through the protection of azides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10424848/
https://www.ncbi.nlm.nih.gov/pubmed/37583567
http://dx.doi.org/10.3389/fchem.2023.1237878
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AT yoshidasuguru synthesisof123triazolesusinggrignardreactionsthroughtheprotectionofazides

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