Novel Synthesis of π-Conjugated Molecules by Cross-Metathesis of Vinylarene and Vinylferrocene with a Schrock Catalyst

Abstract

The novel synthesis of π-conjugated molecules by the cross-metathesis reaction of vinylferrocene with a series of vinylarenes has been investigated with a molybdenum-based Schrock catalyst (CHCMe2Ph)Mo(N-2,6-i-Pr2C6H3)[OCMe(CF3)2]2. The cross-metathesis product, a heterodimer, was readily obtained selectively, and only small amounts of the respective homodimers were formed. The origin of the high selectivity of heterodimer formation was elucidated through the metallacyclobutane intermediate mechanism, the observation of carbenes by in situ 1H NMR, and the reaction products.