Selective oxidative intermolecular carbosulphenylation of aryl alkenes with thiols and nucleophiles via a 1,2-dithioethane intermediate

A periodate lithium-oxidized difunctionalisation of aryl alkenes with thiols and electron-rich aromatics was achieved, selectively affording more than thirty carbosulphenylated products. Both experiments and quantum chemical calculations demonstrated the radical–polar nature of the processes, and that 1,2-dithioethane and thiiranium ions might play the role of intermediates.