Cu-Catalyzed Diarylthiolation of Ynones with Aryl Iodides and Elemental Sulfur: An Access to Tetrasubstituted (Z)-1,2-Bis(arylthio)alkenes and Benzo[b][1,4]dithiines

A copper-catalyzed three-component reaction of ynones, aryl iodides, and elemental sulfur via a syn-addition process is established. The reaction features operational practicality, broad substrate scope, and readily accessible scale-up synthesis by affording a series of (Z)-1,2-bis(arylthio)alkenes in good to excellent yield. Moreover, benzo[b][1,4]dithiines can be also constructed efficiently by using 1,2-diiodobenzene as the coupling partner.

Automated summary

A copper-catalyzed three-component reaction has been established for the synthesis of (Z)-1,2-bis(arylthio)alkenes via a syn-addition process involving ynones, aryl iodides, and elemental sulfur. The reaction shows practicality in operation, broad substrate scope, and the possibility of readily accessible scale-up synthesis with good to excellent yields. Additionally, benzo[b][1,4]dithiines can be efficiently constructed using 1,2-diiodobenzene as the coupling partner.