Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides

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An efficient base, additive and metal-free synthetic methods for α-ketothioamide and α-ketoamide derivatives from readily available sulfoxonium ylides have been described. Sulfoxonium ylides with primary or secondary amines afforded α-ketothioamides in the presence of elemental sulfur, whereas α-ketoamides were produced when I 2 and TBHP were present. The reaction proceeded well at room temperature and generated the corresponding molecules in good to excellent yields. The reaction can be scaled-up and tolerated by a range of functional groups with simple operational procedures.