Palladium-catalyzed coupling and carbonylative coupling of silyloxy compounds with hypervalent iodonium salts

Article abstract of DOI:10.1016/S0040-4039(97)00230-X

Arylation and alkenylation of 1-ethoxy-1-trimetylsilyloxycyclopropane with diphenyliodonium tetrafluoroborate and alkenyliodonium tetrafluoroborate were accomplished by slow addition of silyloxycyclopropane to iodonium salts in the presence of Pd(OAc)₂ (2 mol %) and DME/H₂O (4 : 1) to afford β-substituted ester. Alternatively, carbonylative coupling of silyloxypropane was carried our by slow addition of silyloxypropanes to iodonium salts under CO(1 atm) at room temperature in aqueous medium. The palladium-catalyzed coupling of ketene trimethylsilyl acetals with iodonium sails is also described.