Electrode material promoted dehydrogenative homo-/cross-coupling of weakly activated naphthalenes

Herein, we reported an electrochemical dehydrogenative homo-/cross-coupling of weakly activated naphthalene in the exogenous transition metal- and oxidants-free manner. Benefiting from the microscopic interaction between the reactants and the carbon plate anode, the electropolymerization of aromatic rings was suppressed. And a series of binaphthyl and naphthalene-aryl privileged scaffolds were obtained in 28%-90% yields by homo- or cross-coupling. This C(sp2)-H activation strategy featured atom and step economy as well as the ready scalability.

Automated summary

In this study, an electrochemical dehydrogenative homo-/cross-coupling reaction of weakly activated naphthalene was developed without the involvement of exogenous transition metals and oxidants. The electropolymerization of aromatic rings was suppressed due to the interaction between the reactants and the carbon plate anode. A series of binaphthyl and naphthalene-aryl privileged scaffolds were obtained in yields of 28%-90% through homo- or cross-coupling. This C(sp2)-H activation strategy offers atom and step economy, and can be easily scaled up.