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

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 I2 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.