Ruthenium(II)-Catalyzed <i>Ortho</i>-C–H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

Abstract

Ruthenium(II)-catalyzed <i>ortho</i>-C-H alkylation of naphthylamines with diazo compounds for the synthesis of 2,2-disubstituted π-extended 3-oxindoles has been developed. The method represents the first example of C-H alkylation via carbenoid insertion in water as a sustainable solvent. The procedure includes an inexpensive ruthenium catalyst as well as aqueous media and results in the release of benign N₂. The π-extended 3-oxindole products exhibit favorable antitumor properties and remarkable fluorescent properties in aqueous solution for fluorescent imaging.