Palladium-catalyzed phenyl-selenylation with n-Bu 3SnSePh in one-pot two-step reactions

Abstract

We have studied the Pd-catalyzed cross-coupling reaction of a stannane derived from selenium n-Bu 3SnSePh ( 1) with aryl and perfluoroalkyl iodides. Herein a very efficient one-pot two-step selenylation reaction to form a C–Se bond is reported. Ph 2Se 2 reacts with Na metal in liquid ammonia yielding PhSe − ions. To this solution n-Bu 3SnCl 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%).