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

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 (S-8). 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 S-2 cluster is the most likely active species to participate in the formation of the desired product.