Silver-mediated oxidative C-C bond sulfonylation/arylation of methylenecyclopropanes with sodium sulfinates: facile access to 3-sulfonyl-1,2-dihydronaphthalenes

The novel AgNO3-mediated oxidative sulfonylation/arylation of a C-C sigma-bond in methylenecyclopropanes with sodium sulfinates to synthesize various 3-sulfonylated 1,2-dihydronaphthalenes is reported. This sulfonylation/arylation transformation proceeds via a sequence of sulfonylation, C-C sigma-bond cleavage and intramolecular cyclization, and the experimental results show that the C-C sigma-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for the difunctionalization of C-C bonds with a phenyl ring and a sulfonyl radical via the one-pot construction of a C-S bond and a new C-C bond.