The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization

The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization

4-Sulfonyl-1,2,3-triazole scaffolds possess promising bioactivities and applications as anion binders. However, these structures remain relatively unexplored and efficient synthetic procedures for their synthesis remain desirable. A practical room-temperature, aerobic copper-catalyzed three-componen...

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Bibliographic Details
Main Authors: Max Van Hoof, Santhini Pulikkal Veettil, Wim Dehaen
Format: Article
Language:English
Published: MDPI AG 2021-01-01
Series:Molecules
Subjects:
4-sulfonyl-1,2,3-triazoles
three-component tandem reaction
aerobic oxidation
copper-catalysis
C-H activation
Dimroth azide–enolate cyclization
Online Access:https://www.mdpi.com/1420-3049/26/3/581
Description
Summary:4-Sulfonyl-1,2,3-triazole scaffolds possess promising bioactivities and applications as anion binders. However, these structures remain relatively unexplored and efficient synthetic procedures for their synthesis remain desirable. A practical room-temperature, aerobic copper-catalyzed three-component reaction of aromatic ketones, sodium sulfinates, and azides is reported. This procedure allows for facile access to 4-sulfonyl-1,5-disubstituted-1,2,3-triazoles in yields ranging from 34 to 89%. The reaction proceeds via a sequential aerobic copper(II)chloride-catalyzed oxidative sulfonylation and the Dimroth azide–enolate cycloaddition.
ISSN:1420-3049

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