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22.1.7.2.1.1.1 With Potassium Carbonate and N,N-Diethylaniline as Activators

DOI: 10.1055/sos-SD-122-00021

Tang, R.-Y.Science of Synthesis Knowledge Updates, (20241336.

Potassium carbonate and a catalytic amount of N,N-diethylaniline can promote the sulfurization of amides with phosphorus pentasulfide. N,N-Diethylaniline may react with phosphorus pentasulfide to form an active thionating agent for sulfurization of amides. The sulfurization of aryl and alkyl amides 1 proceeds well in dichloromethane under reflux conditions, providing primary and secondary thioamides 2 in moderate to high yields (Scheme 2).[‌5‌] This method is also applicable to the transformation of esters into thioesters.

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