Ambiphilic vinylcarbenoid reactivity of (alpha-(tributylstannyl)-pi-allyl)palladium(II) species

The ambiphilic vinylcarbenoid reactivity of (alpha-(tributylstannyl)-pi-allyl)palladium(II) species is demonstrated by the reaction of acetoxystannanes with Pd(dba)(2), which promotes electrophilic metal-carbene reactions such as dimerization and cyclopropanation of strained alkenes. On the other hand, Pd(PPh3)(4) and dppe revealed the nucleophilic nature of the dimetallic intermediates through sequential reactions of the carbon-metal bonds with dimethyl malonate.