Solvent Controlled Chemodivergent Sulfonyl Addition into Enynones: Synthesis of α-Furyl Sulfones and Stereodefined Vinyl Sulfones

Sodium salt of aryl sulfinic acid reacts with enynone in a different manner, yielding α-furyl sulfone and stereodefined vinyl sulfone in toluene and EtOH respectively in the presence of ZnCl<sub>2</sub>. The salient features of this protocol include chemoselectivity, broad substrate scope, high efficiency, high yield, and easy purification. The synthetic utilities of the products are demonstrated by cycloaddition and cis-trans photoisomerization reactions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-28
DOI
https://doi.org/10.1021/acs.joc.4c02165
Citations
4
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.00

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article

Solvent Controlled Chemodivergent Sulfonyl Addition into Enynones: Synthesis of α-Furyl Sulfones and Stereodefined Vinyl Sulfones

Ganesh Chandra Nandi, Ramesh Kataria, Padma Priya V. R., Antony Haritha Mercy A
4 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
1.00
article

Solvent Controlled Chemodivergent Sulfonyl Addition into Enynones: Synthesis of α-Furyl Sulfones and Stereodefined Vinyl Sulfones

Ganesh Chandra Nandi, Ramesh Kataria, Padma Priya V. R., Antony Haritha Mercy A
article en
4 citations

Abstract

Sodium salt of aryl sulfinic acid reacts with enynone in a different manner, yielding α-furyl sulfone and stereodefined vinyl sulfone in toluene and EtOH respectively in the presence of ZnCl<sub>2</sub>. The salient features of this protocol include chemoselectivity, broad substrate scope, high efficiency, high yield, and easy purification. The synthetic utilities of the products are demonstrated by cycloaddition and cis-trans photoisomerization reactions.

The Journal of Organic ChemistryVol. 90(1)
National Institute of Technology Tiruchirappalli (IN), Panjab University (IN)
Council of Scientific and Industrial Research, India
Clean water and sanitation
Openalex Percentile: Top 25%
Sulfur-Based Synthesis Techniques
1.00
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Solvent Controlled Chemodivergent Sulfonyl Addition into Enynones: Synthesis of α-Furyl Sulfones and Stereodefined Vinyl Sulfones — Ganesh Chandra Nandi, Ramesh Kataria, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS