Photochemically Mediated Oxidative Cross-coupling of Aminopyrazoles with 1-Thiosugars for the Synthesis of Thioglycosides

By harnessing visible-light excitation of a photocatalyst to initiate a single-electron transfer (SET) process, thereby activating glycosyl thiols to generate thiyl radicals and promote their coupling with aminopyrazoles, this work establishes an efficient photocatalytic strategy for C-S bond construction. This process involves radical addition for thioglycosyl incorporation, followed by oxidative deprotonation to furnish the target products in yields of up to 90%. Consequently, this method enables the efficient synthesis of diverse thioglycosylated pyrazole derivatives under mild conditions, exhibiting a broad substrate scope, excellent functional-group tolerance, and promising scalability, thus providing a green and sustainable synthetic approach.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-24
DOI
https://doi.org/10.1021/acs.joc.6c01248
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photochemically Mediated Oxidative Cross-coupling of Aminopyrazoles with 1-Thiosugars for the Synthesis of Thioglycosides

Nan Yan, Shan Wen, Xian-Hao Wang, Shu-Han Zou et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Photochemically Mediated Oxidative Cross-coupling of Aminopyrazoles with 1-Thiosugars for the Synthesis of Thioglycosides

Nan Yan, Shan Wen, Xian-Hao Wang, Shu-Han Zou, De-Kai Liu
article en

Abstract

By harnessing visible-light excitation of a photocatalyst to initiate a single-electron transfer (SET) process, thereby activating glycosyl thiols to generate thiyl radicals and promote their coupling with aminopyrazoles, this work establishes an efficient photocatalytic strategy for C-S bond construction. This process involves radical addition for thioglycosyl incorporation, followed by oxidative deprotonation to furnish the target products in yields of up to 90%. Consequently, this method enables the efficient synthesis of diverse thioglycosylated pyrazole derivatives under mild conditions, exhibiting a broad substrate scope, excellent functional-group tolerance, and promising scalability, thus providing a green and sustainable synthetic approach.

The Journal of Organic Chemistry
Jiangxi University of Water Resources and Electric Power (CN), Jiangxi Normal University (CN)
Openalex Percentile: Top 26%
Radical Photochemical Reactions
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