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Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

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Author(s)
Leypold, Mario
•
D’Angelo, Kyan A
•
Movassaghi, Mohammad
Date Issued
2020
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Leypold, Mario, D’Angelo, Kyan A and Movassaghi, Mohammad. 2020. "Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents." Organic Letters, 22 (22).
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Final published version
Abstract
© 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.
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DOI of Published Version
10.1021/ACS.ORGLETT.0C03160
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