Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

© 2020 American Chemical Society The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en rout...

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Bibliographic Details
Main Authors: Leypold, Mario (Author), D'Angelo, Kyan A (Author), Movassaghi, Mohammad (Author)
Format: Article
Language:English
Published: American Chemical Society (ACS), 2022-03-10T20:13:13Z.
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Summary:© 2020 American Chemical Society The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies identified activated sulfoxides as promoters of the desired transformation and enabled the extension of the methodology from benzylic to aliphatic amide substrates.