Ring-Closing Disulfenylation of Alkenoic Thioester

This study demonstrated for the first time that alkenoic thioesters can be effectively used as nucleophiles in ring-closing disulfenylation reactions. Our investigation revealed that the reaction in hexafluoroisopropanol with an electrophilic sulfur reagent significantly enhances the product yield. We gathered experimental and theoretical evidence to support the superiority of thioesters over the traditionally used benzyl sulfide. Additionally, we explored the substrate scope and identified various factors affecting the reaction selectivity and yield.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-26
DOI
https://doi.org/10.1021/acs.joc.4c02180
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.50

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article

Ring-Closing Disulfenylation of Alkenoic Thioester

Hiroki Shigehisa, Miari Kurihara, Kanaru Sasaki
2 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.50
article

Ring-Closing Disulfenylation of Alkenoic Thioester

Hiroki Shigehisa, Miari Kurihara, Kanaru Sasaki
article en
2 citations

Abstract

This study demonstrated for the first time that alkenoic thioesters can be effectively used as nucleophiles in ring-closing disulfenylation reactions. Our investigation revealed that the reaction in hexafluoroisopropanol with an electrophilic sulfur reagent significantly enhances the product yield. We gathered experimental and theoretical evidence to support the superiority of thioesters over the traditionally used benzyl sulfide. Additionally, we explored the substrate scope and identified various factors affecting the reaction selectivity and yield.

The Journal of Organic ChemistryVol. 89(20)
Musashino University (JP)
Naito Foundation, Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 39%
Sulfur-Based Synthesis Techniques
0.50
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