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Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
preprintsubmitted on 04.08.2020, 14:06 and posted on 05.08.2020, 12:33 by Mario Leypold, Kyan A. D’Angelo, Mohammad Movassaghi
The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies support the critical role of activated sulfoxides that promote the desired transformation. For benzylic amide substrates, a single-step protocol featuring a spontaneous dealkylation step of a sulfonium ion intermediate was developed.