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

Rina Namioka; Minori Suzuki; Minori Suzuki; Suguru Yoshida

doi:10.3389/fchem.2023.1237878

Frontiers in Chemistry (Jul 2023)

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

Rina Namioka,
Minori Suzuki,
Minori Suzuki,
Suguru Yoshida

Affiliations

Rina Namioka: Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, Tokyo, Japan
Minori Suzuki: Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, Tokyo, Japan
Minori Suzuki: Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), Tokyo, Japan
Suguru Yoshida: Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, Tokyo, Japan

DOI: https://doi.org/10.3389/fchem.2023.1237878
Journal volume & issue: Vol. 11

Abstract

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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.

Published in Frontiers in Chemistry

ISSN: 2296-2646 (Online)
Publisher: Frontiers Media S.A.
Country of publisher: Switzerland
LCC subjects: Science: Chemistry
Website: http://journal.frontiersin.org/journal/chemistry

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