Regioselective Mg-Promoted C-Acylation of Stilbene and Acenaphthylene Derivatives

Abstract

Treatment of stilbene and acenaphthylene derivatives with Mg turnings in the presence of aliphatic acid anhydrides and trimethylsilyl chloride (TMSCl) in N,N-dimethylformamide (DMF) brought about a facile and efficient cross-coupling to give C-acylation products in moderate to good yields. The reaction may be initiated by electron transfer from magnesium to the carbon-carbon double bonds of the substrates to generate the corresponding anionic species which are subsequently subjected to regioselective electrophilic acylation with acid anhydrides.