Direct Synthesis of Various Thioesters from Acyl Fluorides and Thiosilanes through the Assistance of a Si–F Bond Formation

Herein it is described that the coupling reactions of aromatic and aliphatic acyl fluorides with phenyl trimethylsilyl sulfide proceeded smoothly under neat conditions to produce thioester derivatives. The addition of a catalytic amount of typical bases, such as triethylamine (Et<sub>3</sub>N) and potassium butoxide (KO<sup><i>t</i></sup>Bu), effectively activates thiosilanes, which could facilitate the coupling reactions of aroyl fluorides with a variety of aryl/alkyl thiosilanes containing an alkyl group, a halogen, an ester, or a heterocyclic ring to produce a variety of thioesters in practical yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-02
DOI
https://doi.org/10.1021/acs.joc.5c01677
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.94
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article

Direct Synthesis of Various Thioesters from Acyl Fluorides and Thiosilanes through the Assistance of a Si–F Bond Formation

Kento Ishida, Norio Sakai, Ryuki Takeuchi
1 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.94
article

Direct Synthesis of Various Thioesters from Acyl Fluorides and Thiosilanes through the Assistance of a Si–F Bond Formation

Kento Ishida, Norio Sakai, Ryuki Takeuchi
article en
1 citations

Abstract

Herein it is described that the coupling reactions of aromatic and aliphatic acyl fluorides with phenyl trimethylsilyl sulfide proceeded smoothly under neat conditions to produce thioester derivatives. The addition of a catalytic amount of typical bases, such as triethylamine (Et<sub>3</sub>N) and potassium butoxide (KO<sup><i>t</i></sup>Bu), effectively activates thiosilanes, which could facilitate the coupling reactions of aroyl fluorides with a variety of aryl/alkyl thiosilanes containing an alkyl group, a halogen, an ester, or a heterocyclic ring to produce a variety of thioesters in practical yields.

The Journal of Organic ChemistryVol. 90(41)
Tokyo University of Science (JP)
Openalex Percentile: Top 21%
Sulfur-Based Synthesis Techniques
0.94
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Direct Synthesis of Various Thioesters from Acyl Fluorides and Thiosilanes through the Assistance of a Si–F Bond Formation — Kento Ishida, Norio Sakai, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS