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Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides.

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Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base… Click to show full abstract

Reactions of secondary thioamides with diaryliodonium salts under basic, transition metal-free conditions resulted in chemoselective S-arylation to provide aryl thioimidates in good to excellent yields. Equimolar amounts of thioamide, base and diaryliodonium salt were sufficient to obtain a diverse selection of products within short reaction times. Reactions with thiolactams delivered N-arylated thioamides in good yield at room temperature.

Keywords: metal free; aryl thioimidates; transition metal; chemoselective arylation

Journal Title: Chemical communications
Year Published: 2018

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