Reaction of arylboronic acids and their derivatives with lead tetra-acetate. The generation of aryl–lead triacetates, and meta- and para-phenylenebis(lead triacetate), in situ for electrophilic arylation

Abstract

Arylboronic acids and some of their derivatives have been found to undergo a rapid boron–lead exchange with lead tetra-acetate. In the presence of a catalytic amount of mercury(II) acetate, the reaction produces mainly the aryl–lead triacetate, and it has been developed as a convenient method for in situ generation of these useful electrophilic C-arylating reagents. The reaction allows the generation for the first time of meta- and para-phenylenebis(lead triacetate), compounds which behave as meta- and para-phenylene dication equivalents.