One-pot synthesis of sulfonylmethyl phthalides <i>via</i> K <sub>2</sub> S <sub>2</sub> O <sub>8</sub> /DMSO-mediated methylenylation/sulfonylation of eudesmic acid with sulfinates

A K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/DMSO-mediated one-pot reaction of eudesmic acid with sodium sulfinates was developed for the synthesis of various sulfonylmethyl trioxygenated phthalides <i>via</i> double methylenation and sulfonylation pathways. In this effective reaction, dimethyl sulfoxide was used as both a solvent and a methylene source through the formation of one carbon-sulfur single bond, one carbon-oxygen single bond, and two carbon-carbon single bonds under open-vessel conditions.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00632e
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.87
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article

One-pot synthesis of sulfonylmethyl phthalides via K 2 S 2 O 8 /DMSO-mediated methylenylation/sulfonylation of eudesmic acid with sulfinates

Chung‐Jen Ou, Meng‐Yang Chang
2 citations
Organic & Biomolecular Chemistry
Sulfur-Based Synthesis Techniques
1.87
article

One-pot synthesis of sulfonylmethyl phthalides via K 2 S 2 O 8 /DMSO-mediated methylenylation/sulfonylation of eudesmic acid with sulfinates

Chung‐Jen Ou, Meng‐Yang Chang
article en
2 citations

Abstract

A K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>/DMSO-mediated one-pot reaction of eudesmic acid with sodium sulfinates was developed for the synthesis of various sulfonylmethyl trioxygenated phthalides <i>via</i> double methylenation and sulfonylation pathways. In this effective reaction, dimethyl sulfoxide was used as both a solvent and a methylene source through the formation of one carbon-sulfur single bond, one carbon-oxygen single bond, and two carbon-carbon single bonds under open-vessel conditions.

Organic & Biomolecular ChemistryVol. 23(27)
Kaohsiung Medical University (TW), National Pingtung University of Science and Technology (TW), Kaohsiung Medical University Chung-Ho Memorial Hospital (TW)
Clean water and sanitation
Openalex Percentile: Top 15%
Sulfur-Based Synthesis Techniques
1.87
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