An efficient and green procedure for transformation of thiols to disulfides and thioamides in AGA8 aqueous micelles

Abstract

A variety of novel non-ionic, sugar-based surfactants was synthesized to promote the construction of disulfides and thioamides under mild conditions in H₂O. TEM and DLS characterization confirmed that spherical micelles formed using AGA8 aqueous solution could provide a miniature reaction site for thiol substrates with elemental sulfur (S₈). With this green protocol, both disulfides and thioamides could be obtained in moderate to excellent yields with a high level of tolerance of various functional groups. The disulfides were found as intermediates for the synthesis of thioamide from thiol, and the resulting quantum chemical calculations show that an S₂ cluster is the most likely active species to participate in the formation of the desired product.