Oxytrifluoromethylselenylation of olefins with N–SeCF3 saccharin as trifluoromethylselenylated reagent

This work presents a new approach for the oxytrifluoromethylselenolation of olefins using N–SeCF3 saccharin as an electrophilic trifluoromethylselenolation reagent, alcohols as nucleophiles, and dichloromethane as the solvent. The approach employed in mild reaction conditions, free of transition met...

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Veröffentlicht in:Tetrahedron 2025-02, Vol.171, p.134419, Article 134419
Hauptverfasser: Xie, Ke-Yi, Zhu, Yi-Nuo, Shi, Ming-Hui, Wang, Ze-Dong, Zhang, Cong-Cong, Wang, Zhen-Tao
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Sprache:eng
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Zusammenfassung:This work presents a new approach for the oxytrifluoromethylselenolation of olefins using N–SeCF3 saccharin as an electrophilic trifluoromethylselenolation reagent, alcohols as nucleophiles, and dichloromethane as the solvent. The approach employed in mild reaction conditions, free of transition metals and other additives, and showed excellent application to various substrates as well as compatibility with functional groups. A proposed mechanism was investigated by control experiments. [Display omitted] •A novel mild olefinic oxytrifluoromethylselenylation using N–SeCF3 saccharin without catalyst or any additives was developed.•This new method performed wide substrate scope.•A proposed mechanism contained selenium onium ion was propounded.
ISSN:0040-4020
DOI:10.1016/j.tet.2024.134419