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

Article abstract of DOI:10.1016/0022-328X(93)80305-U

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