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Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

preprint
submitted on 04.08.2020 and posted on 05.08.2020 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.

Funding

NIH-NIGMS (GM074825)

Austrian Science Fund (FWF): J3930-N34

Natural Sciences and Engineering Research Council of Canada (NSERC): PGS-D3

History

Email Address of Submitting Author

movassag@mit.edu

Institution

MIT

Country

USA

ORCID For Submitting Author

0000-0003-3080-1063

Declaration of Conflict of Interest

None

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