Ruthenium-Catalyzed Activation of Nonpolar C-C Bonds via π-Coordination-Enabled Aromatization.

Activation of C-C bonds allows editing of molecular skeletons, but methods for selective activation of nonpolar C-C bonds in the absence of a chelation effect or a driving force derived from opening of a strained ring are scarce. Herein, we report a method for ruthenium-catalyzed activation of nonpolar C-C bonds of pro-aromatic compounds by means of π-coordination-enabled aromatization. This method was effective for cleavage of C-C(alkyl) and C-C(aryl) bonds and for ring-opening of spirocyclic compounds, providing an array of benzene-ring-containing products. The isolation of a methyl ruthenium complex intermediate supports a mechanism involving ruthenium-mediated C-C bond cleavage.