Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation

Md Mahbubur Rahman, Michal Szostak

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


The direct synthesis of sulfoxonium ylides from amides by selective N-C(O) cleavage is presented. The reaction proceeds through the nucleophilic addition of dimethylsulfoxonium methylide to the amide bond in acyclic twisted amides under exceedingly mild room temperature conditions. A variety of amides can be employed, and the protocol can be applied to the late-stage derivatization of pharmaceuticals. Mechanistic studies outline the relative order of reactivity of amides.

Original languageEnglish (US)
Pages (from-to)4818-4822
Number of pages5
JournalOrganic letters
Issue number12
StatePublished - Jun 18 2021

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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