Highly Reactive Hydrocarbon Soluble Alkylsodium Reagents for Benzylic Aroylation of Toluenes using Weinreb Amides

Deaggregating the alkyl sodium NaCH2SiMe3 with polydentate nitrogen ligands enables preparation and characterisation of new, hydrocarbon soluble chelated alkylsodium reagents. Equipped significantly enhanced metalating power over their organolithium counterparts, these systems can promote controlled sodiation weakly acidic benzylic C−H bonds from a series toluene derivatives under mild stoichiometric conditions. This has been demonstrated through aroylation toluenes Weinreb amides, that delivers wide range 2-arylacetophenones in good to excellent yields. Success isolating determining structures key organometallic intermediates provided useful mechanistic insight into new sodium-mediated transformations.