Ring-Closing Disulfenylation\nof Alkenoic Thioester

This\nstudy demonstrated for the first time that alkenoic thioesters\ncan be effectively used as nucleophiles in ring-closing disulfenylation\nreactions. Our investigation revealed that the reaction in hexafluoroisopropanol\nwith an electrophilic sulfur reagent significantly enhances the product\nyield. We gathered experimental and theoretical evidence to support\nthe superiority of thioesters over the traditionally used benzyl sulfide.\nAdditionally, we explored the substrate scope and identified various\nfactors affecting the reaction selectivity and yield.

Publication Details

Journal
Figshare
Published
2024-09-26
DOI
https://doi.org/10.1021/acs.joc.4c02180.s001
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Ring-Closing Disulfenylation\nof Alkenoic Thioester

Figshare
Sulfur-Based Synthesis Techniques
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Ring-Closing Disulfenylation\nof Alkenoic Thioester

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Abstract

This\nstudy demonstrated for the first time that alkenoic thioesters\ncan be effectively used as nucleophiles in ring-closing disulfenylation\nreactions. Our investigation revealed that the reaction in hexafluoroisopropanol\nwith an electrophilic sulfur reagent significantly enhances the product\nyield. We gathered experimental and theoretical evidence to support\nthe superiority of thioesters over the traditionally used benzyl sulfide.\nAdditionally, we explored the substrate scope and identified various\nfactors affecting the reaction selectivity and yield.

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Sulfur-Based Synthesis Techniques
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Ring-Closing Disulfenylation\nof Alkenoic Thioester · Figshare (2024) | TGRS Research Map | TGRS