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

ABSTRACT: 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.

SUBMITTER: Namioka R

PROVIDER: S-EPMC10424848 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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

Namioka Rina R Suzuki Minori M Yoshida Suguru S

Frontiers in chemistry 20230731

An efficient method to prepare organomagnesium intermediates having a protected azido group is reported. Protection of azido groups with di-(<i>tert</i>-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 enable ...[more]

PMID: 37583567

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