Chinese Journal of Chemistry· 2026Q1
Photoinduced Trifluoromethyl‐ and Difluoromethyl‐Chalcogenation of α‐Diazo Compounds
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- 2026year
Short summary
A novel photochemical strategy enables mild and green synthesis of trifluoromethylthiolated and difluoromethylthiolated compounds from α‐diazo compounds, achieving up to >99% yield across 37 examples.
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Key points
- Developed a novel photochemical strategy for trifluoromethyl- and difluoromethyl-chalcogenation of α‐diazo compounds.
- Achieved broad substrate scope and good functional group tolerance with yields up to >99% for 37 examples.
- Demonstrated gram-scale synthesis with a 69% yield (1.45 g).
- Products showed promising antibacterial activity.
- Mechanistic study suggests a cascade process via oxonium species.
AI-generated from the title and abstract; the full text is not read.
Abstract
Comprehensive Summary Organofluorides, including trifluoromethylthiolated compounds, play an important role in pharmaceuticals, agrochemicals and materials science. Although the synthesis of these organofluorides has been well studied, harsh conditions and specific substrates are usually involved, which limited the development of this field. Herein, we report a novel protocol to construct highly functionalized trifluoromethylthiolated and derived scaffolds via the trifluoromethyl‐ and difluoromethyl‐chalcogenation of α‐diazo compounds under mild and green conditions using a photochemical strategy. This multicomponent reaction exhibits broad substrate scope and good functional group tolerance (37 examples, up to >99% yield), which could be applied to late‐stage modification of complex natural products. Additionally, the gram‐scale synthesis and antibacterial assays were carried out to explore the application of this transformation, and the results showed good scalability (1.45 g, 69% yield) as well as promising antibacterial activity. Moreover, the mechanistic study indicates a cascade process via oxonium species.
The authors' abstract, as published at the source. Chinese Journal of Chemistry, 2026 · DOI ↗
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Field: Pharmaceutical Science
Pharmaceutical SciencePharmacology, Toxicology and Pharmaceutics