Chalcogenide-Catalyzed Intermolecular Electrophilic Thio- and Halofunctionalization of gem-Difluoroalkenes: Construction of Diverse Difluoroalkyl Sulfides and Halides

Thio- and halodifluoromethylated compounds are an important class of compounds in medicinal chemistry and organic synthesis. Herein, we report a facile method for the construction of these compounds via chalcogenide-catalyzed intermolecular electrophilic thio- and halofunctionalization of gem-difluo...

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Veröffentlicht in:Organic letters 2020-10, Vol.22 (19), p.7581-7587
Hauptverfasser: Jiang, Quanbin, Liang, Yaoyu, Zhang, Yuanyuan, Zhao, Xiaodan
Format: Artikel
Sprache:eng
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Zusammenfassung:Thio- and halodifluoromethylated compounds are an important class of compounds in medicinal chemistry and organic synthesis. Herein, we report a facile method for the construction of these compounds via chalcogenide-catalyzed intermolecular electrophilic thio- and halofunctionalization of gem-difluoroalkenes. Simple treatment of gem-difluoroalkenes with electrophilic sulfur/halogen reagents and various O- or N-nucleophiles affords diverse multifunctionalized thio- and halodifluoromethylated compounds. This reaction features a relatively broad substrate scope, good functional group tolerance, and mild reaction conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02784