Chain-length-dependent reactivity of alkenyl phosphates in ruthenium-catalyzed cross-metathesis

Abstract

We report a chain-length-dependent reactivity pattern in the cross-metathesis of alkenyl phosphates catalyzed by the second-generation Grubbs catalyst (GII). While vinyl phosphates undergo unproductive decomposition to generate a ruthenium-carbide complex, extending the alkyl spacer restores productive cross-metathesis. DFT studies rationalize this transformation to occur via a proton-coupled phosphate elimination mechanism.