Palladium-catalyzed phenyl-selenylation with n-Bu3SnSePh in one-pot two-step reactions

We have studied the Pd-catalyzed cross-coupling reaction of a stannane derived from selenium n-Bu₃SnSePh (1) with aryl and perfluoroalkyl iodides. Herein a very efficient one-pot two-step selenylation reaction to form a C-Se bond is reported. Ph₂Se₂ reacts with Na metal in liquid ammonia yielding PhSe⁻ ions. To this solution n-Bu₃SnCl was added to afford 1, which was introduced in the palladium-catalyzed coupling reaction without isolation. These reactions afford functionalized diarylselenides and phenylperfluroalkyl selenides from good to high yields (38-98%).