InI₃-Catalyzed Synthesis of Thioethers Using Thiosilanes

Key words

indium - thiosilanes - thioethers - alkyl acetates

Significance

Herein, the authors disclose an ­indium triiodide catalyzed substitution of the ­acetoxy group in various alkyl acetates using thio­silanes. This method successfully converts various primary, secondary and tertiary alkyls, as well as propargylic, allylic and benzylic systems into the appropriate thioethers with a high functional group tolerance.

Comment

The corresponding thioethers are obtained in good to excellent yields. In the case of primary alkyl acetates and α-acetoxy carbonyl derivatives, substitution is supposed to proceed via an S_N2 reaction, whereas benzylic, allylic, porpargylic and secondary or tertiary alkyl acetates are substituted by an S_N1-type mechanism.