Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents | Zendy

Mario Leypold | Zendy; Kyan A. D’Angelo | Zendy; Mohammad Movassaghi | Zendy

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Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

Author(s) -

Mario Leypold,

Kyan A. D’Angelo,

Mohammad Movassaghi

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c03160

Subject(s) - sulfidation , chemistry , reagent , sulfonium , amide , electrophile , sulfoxide , sulfide , combinatorial chemistry , organic chemistry , catalysis , salt (chemistry)

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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