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

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Jan 27

PMID 33499353

Authors

Max Van Hoof

Santhini Pulikkal Veettil

Wim Dehaen

Affiliations

Soon will be listed here.

Abstract

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.

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