Organic Letters· 2026Q1
Insertion into Donor–Acceptor Cyclopropanes with Carbon–Sulfur Moieties Derived from Sulfoxonium Ylides and Elemental Sulfur
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- Q1SCImago
- 2026year
Short summary
A new method enables the (3+2) cycloaddition of donor–acceptor cyclopropanes (DACs) with carbon–sulfur moieties, forming tetrahydrothiophenes without Lewis acid catalysis.
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Key points
- Developed a new method for (3+2) cycloaddition of DACs with carbon–sulfur moieties.
- Utilizes α-carbonyl sulfoxonium ylides and elemental sulfur to form the carbon–sulfur unit in situ.
- Reaction proceeds without Lewis acid catalysis.
- Successfully synthesized α-monosubstituted tetrahydrothiophenes with diverse functional groups.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract The (3 + 2) cycloaddition of donor–acceptor cyclopropanes (DACs) with carbon–sulfur 2π components has become an emerging method to rapidly assemble tetrahydrothiophenes. Starting materials donating the carbon–sulfur unit are often isolated from thionation of carbonyls or carboxylic acid derivatives. Herein we report a method for the cycloaddition of DACs with carbon–sulfur moieties presumably formed in situ via β-sulfuration of α-carbonyl sulfoxonium ylides with elemental sulfur. The insertion occurred without the assistance of Lewis acid, perhaps due to the strongly polarized carbon–sulfur-containing intermediate. The hitherto challenging α-monosubstituted tetrahydrothiophenes were obtained with a wide range of tolerated functionalities.
The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry