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

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journal contribution
posted on 19.06.2020, 13:05 by Xiaogang Wang, Jin Zhang, Yuan He, Di Chen, Chao Wang, Fangzhou Yang, Weitao Wang, Yangmin Ma, Michal Szostak
Ruthenium­(II)-catalyzed ortho-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.