Science of Synthesis

Li, X.; Song, Q., Science of Synthesis Knowledge Updates, (2024) 1, 315.

In addition to phosphorus decasulfide and Lawesson’s reagent (Section ‌22.1.3.3.1‌), some other sulfur-containing compounds can also be employed as thionating reagents. In 2022, Gaonkar and co-workers found that the simple and commercially available inorganic salt potassium thiocyanate (KSCN) could act as a thionating reagent for carboxylic esters ‌5‌ under microwave irradiation to give thionoesters ‌6‌ (‌Scheme 3‌).[‌4‌] The probable mechanism for this reaction involves the formation of an oxathietane intermediate ‌7‌, which then undergoes ring opening to finally furnish the target thionoesters along with the side product potassium cyanate.

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References