Synthesis
Thioesters have been prepared in many ways, but the main route involves condensation of thiols and carboxylic acids in the presence of dehydrating agents:
- RSH + R'CO2H → RSC(O)R' + H2O
A typical dehydration agent is DCC or related reagents. Acid anhydrides and some lactones also react with thiols in the presence of base.
Thioesters can be conveniently prepared from alcohols by the Mitsunobu reaction, using thioacetic acid.
They also arise via carbonylation of alkynes and alkenes in the presence of thiols.
Read more about this topic: Thioester
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