Allylic Substitution versus Suzuki Cross‐Coupling: Capitalizing on Chemoselectivity with Bifunctional Substrates

One catalyst, two reactions—a tale of chemoselectivity: Given the choice between an allylic acetate and a vinylboronate ester, palladium preferentially reacts with the allylic acetate to give the allylic substitution product. In the presence of an aryl bromide and base, Suzuki cross-coupling subsequently ensues to afford allylic amines (see scheme; pin=pinacol, THF=tetrahydrofuran).