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Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.

ABSTRACT: 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.

SUBMITTER: Leypold M

PROVIDER: S-EPMC7680396 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.

Leypold Mario M D'Angelo Kyan A KA Movassaghi Mohammad M

Organic letters 20201013 22

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. ...[more]

PMID: 33048547

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