A MILD AND EFFICIENT SRN1 APPROACH TO DIARYL SULFIDES FROM ARENEDIAZONIUM TETRAFLUOROBORATES

Article abstract of DOI:10.1016/S0040-4020(01)87556-6

The reaction between arenediazonium tetrafluoroborates and sodium arenethiolates in Me2SO at 25 deg C represent an efficient access to diaryl sulfides.A number of evidences suggest the occurance of a radical, radical-anion SRN1 mechanism, the arenethiolate acting both as electron donor and as aryl-radical trapping nucleophile.Valuable improvements with respect to recent SRN1 syntheses of diaryl sulfides from haloarenes are represented, inter alia, by the compatibility of both electron-withdrawing and relasing substituents as well as by the intensivity to steric hindrance in the diazonium salt.When the arenediazonium ion bears another SRN1 leaving group (such as Cl, Br, or I) disubstitution products are predominantly formed.