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

1993; Elsevier BV; Volume: 443; Issue: 2 Linguagem: Inglês

10.1016/0022-328x(93)80305-u

1872-8561

Chan Sik Cho, Koichi Itotani, Sakae Uemura,

Catalytic C–H Functionalization Methods

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.