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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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

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record_format	Article
spelling	doaj-290ea207e7ee45fcbf8ce20eb2231bf92021-01-23T00:05:37ZengMDPI AGMolecules1420-30492021-01-012658158110.3390/molecules26030581The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth CyclizationMax Van Hoof0Santhini Pulikkal Veettil1Wim Dehaen2Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, BelgiumMolecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium4-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.https://www.mdpi.com/1420-3049/26/3/5814-sulfonyl-1,2,3-triazolesthree-component tandem reactionaerobic oxidationcopper-catalysisC-H activationDimroth azide–enolate cyclization
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Max Van Hoof Santhini Pulikkal Veettil Wim Dehaen
spellingShingle	Max Van Hoof Santhini Pulikkal Veettil Wim Dehaen The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization Molecules 4-sulfonyl-1,2,3-triazoles three-component tandem reaction aerobic oxidation copper-catalysis C-H activation Dimroth azide–enolate cyclization
author_facet	Max Van Hoof Santhini Pulikkal Veettil Wim Dehaen
author_sort	Max Van Hoof
title	The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization
title_short	The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization
title_full	The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization
title_fullStr	The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization
title_full_unstemmed	The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization
title_sort	three-component synthesis of 4-sulfonyl-1,2,3-triazoles via a sequential aerobic copper-catalyzed sulfonylation and dimroth cyclization
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2021-01-01
description	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.
topic	4-sulfonyl-1,2,3-triazoles three-component tandem reaction aerobic oxidation copper-catalysis C-H activation Dimroth azide–enolate cyclization
url	https://www.mdpi.com/1420-3049/26/3/581
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The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization

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