Transition-metal-free decarboxylative thiolation of stable aliphatic carboxylates

A transition-metal-free decarboxylative thiolation protocol is reported in which primary, secondary, tertiary (hetero)aryl acetates and alpha-CN substituted acetates undergo the decarboxylative thiolation smoothly, to deliver a variety of functionalized aryl alkyl sulfides in moderate to excellent yields. Aryl diselenides are also amenable substrates for construction of C-Se bonds under the simple and mild reaction conditions. Moreover, the protocol is successfully applied to the late-stage modification of pharmaceutical carboxylates with satisfactory chemoselectivity and functional-group compatibility.

Automated summary

A transition-metal-free decarboxylative thiolation protocol is introduced for the synthesis of a variety of functionalized aryl alkyl sulfides and C-Se bond compounds, which is successfully applied for the modification of pharmaceutical carboxylates.