Ultrasound-Accelerated Synthesis of Asymmetrical Thiosulfonate S-Esters by Base-Promoted Reaction of Sulfonyl Chlorides with Thiols

GRAPHICAL ABSTRACT

Abstract

Amberlyst A-26, Mg-Al hydrotalcite, potassium fluoride absorbed on alumina, triethylamine and pyridine have been tested as base catalysts and reagents for the reaction of sulfonyl chlorides with thiols to prepare thiosulfonate S-esters. The reactions were performed under solvent-free conditions or with a minimum amount of solvent assisted by magnetic stirring, ultrasound irradiation and microwave irradiation. Ultrasound irradiation has good effects on the synthesis of sterically hindered thiosulfonate S-esters in solvent-free media as well as in a minimum amount of anhydrous diethyl ether.

Keywords:

• Thiosulfonates
• thiols
• sulfonyl chlorides
• triethylamine
• ultrasound irradiation