Controllable cross-coupling of thiophenols with dichloromethane mediated by consecutively paired electrolysis

Abstract

Chloroalkanes are important building blocks in the synthesis, but their use in redox chemistry is limited by their negative reduction potentials. Electrosynthesis can precisely control the reaction energy just by adjusting the current or voltage to achieve the selectivity of regulation. In this study, the consecutively paired electrolytic-mediated controllable radical cross-coupling of thiophenols with dichloromethane was developed to deliver the dithioacetals, sulfides, and sulfoxides in the absence of electrochemical mediator conditions. It features broad substrate scope, simple operation, gram-scale synthesis, and is eco-friendly. Mechanistic studies reveal that this electrochemical reaction is radical-induced cross-coupling of thiophenols with dichloromethane.

Keywords

• Paired electrolytic
• Cross-coupling
• Dichloromethane
• Thiophenols
• Dithioacetals
• Sulfoxides