Sodium tetraphenylborate as a phenylating reagent in the palladium-catalyzed phenylation of alkenes and acid chlorides

Sodium tetraphenylborate (NaBPh₄) reacts with terminal alkenes in acetic acid at 25°C in the presence of a catalytic amount of palladium(II) acetate together with silver acetate as a re-oxidant to give the corresponding phenylated alkenes in 22-87% yield. It also reacts with acid chlorides in tetrahydrofuran (THF) at 25°C in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) to give the corresponding phenyl ketones in 51-100% yield. Carbonylation of the borate with 1-30 atm carbon monoxide (CO) in methanol at 25°C in the presence of palladium(II) acetate or sodium chloropalladate (Na₂PdCl₄) affords a low yield (9-30%) of benzophenone and methyl benzoate, a higher pressure favoring the formation of the latter.