Copper-Catalyzed C(sp³)–H Azidation of 1,3-Dihydro-2H-indol-2-ones Under Mild Conditions

◊These authors contributed equally to this work.

Abstract

A simple and economical synthesis of 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones has been realized under mild conditions through copper-catalyzed C(sp³)–H azidation of the corresponding 1,3-dihydro-2H-indol-2-ones with trimethylsilyl azide. The reaction proceeds by an efficient pathway involving the addition of a N₃ radical to the enol tautomer and consecutive C(sp³)−N bond formations. The method is valuable because of its mild reaction conditions, short reaction times, and broad substrate scope, and because of the rich biological activity of the resulting 3-substituted 3-azido-1,3-dihydro-2H-indol-2-one products.

Keywords

copper catalysis - radical reaction - azidoindolinones - indolinones - azidation - trimethylsilyl azide

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