Oxone-Mediated Radical C–C Bond Acetmethylation/Arylation of Methylenecyclopropanes and Vinylcyclopropanes with α-Alkyl Ketones: Facile Access to Oxoalkyl-Substituted 3,4-Dihydronaphthalenes

An efficient oxone-mediated radical carbon-carbon σ-bond acetmethylation/arylation of methylenecyclopropanes with α-C(sp³)-H bonds of ketones is described for the preparation of 2-(2-oxopropyl)-3,4-dihydronaphthalenes. This acetmethylation/arylation undergoes a series of α-C(sp³)-H bond activation, carbon-carbon double bond acetmethylation, carbon-carbon σ-bond cleavage, and cyclization with intramolecular aromatic ring. The experimental result indicates that the carbon-carbon σ-bond acetmethylation/arylation transformation contains a radical process. The difunctionalization method can also be applied to carbon-carbon σ-bond acetmethylation/arylation of vinylcyclopropanes with ketones. This strategy offers an efficient and convenient method for acetmethylation/arylation of a carbon-carbon σ-bond with a α-carbonyl radical and an aromatic carbon in one pot, building two new carbon-carbon bonds.