Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

Leypold, Mario; D’Angelo, Kyan A; Movassaghi, Mohammad

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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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Creative Commons Attribution 4.0 International license

https://creativecommons.org/licenses/by/4.0/

Persistent DSpace Link

https://hdl.handle.net/1721.1/141143

DOI of Published Version

10.1021/ACS.ORGLETT.0C03160