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

Organic Letters
Md Mahbubur Rahman, Michal Szostak

Abstract

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.

References

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Oct 22, 2020·Organic & Biomolecular Chemistry·Giorgiana Denisa BisagLuca Bernardi

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