Rapid and Convenient Thioester Synthesis Under Phase-Transfer Catalysis Conditions

Abstract

Various thioesters were obtained through an efficient phase-transfer catalysis method, by treating several thiophenols with different acyl chlorides, in a biphasic system composed of 10% aqueous NaOH and dichloromethane in the presence of tetrabutylammonium chloride. The thiolation reaction was complete in only 5 minutes, at 0°C.

Keywords:

• S-Acylation
• phase transfer catalysis
• tetrabutylammonium chloride
• thioesters

Notes

^a BnCl = tetrabutylammonium chloride; BnBr = tetrabutylammonium bromide.

^b Not attempted.

^c Reaction time = 20 min.

*BnC, 3 mmol; thiol, 3 mmol; (CH₂)_n(COCl)₂, 1.5 mmol; 20 mL 10% NaOH aq., 20 mL CH₂Cl₂; 0°C, 5 min.