Electroreductive Desulfurative Transformations with Thioethers As Alkyl Radical Precursor

Abstract

Thioethers are highly prevalent functional groups in organic compounds of natural andsynthetic origin but remain remarkably underexplored as starting materials indesulfurative transformations. As such, new synthetic methods are highly desirable tounlock the potential of the compound class and electrochemistry is an ideal tool toenable new reactivity and selectivity under mild conditions.We target aryl alkyl thioethers, which outperformes their well-established sulfoneanalogue, to form C-C bonds through the reactive intermediate. Cleaving the bond inthe precense of a hydrogen donor results in the dehydrosulfurisation product. Doing thesame reaction in the precense of CO2 or electron deficient alkene results either in thecarboxylic acid or the C(sp3)–C(sp3) product. Figure 1