Abstract
Abstract A convenient aerobic oxidative hydroxylation of 3-substituted oxindoles under mild reaction conditions is described herein. This process was accomplished by the activation of molecular oxygen in the air in the presence of a photocatalyst under the irradiation of visible light. The desired product was delivered in up to 89% yield without the addition of base or stoichiometric oxidant.
Highlights
The 3-substituted-3-hydroxy-2-oxindole framework is a privileged motif that is abundant in naturally occurring alkaloids and biologically active products [1,2]
Discovered in Hibiscus moscheutos L methyl 2-(3-hydroxy2-oxoindolin-3-yl)acetate acted as an anti-oxidant [4]. (R)-(+)-3-cyanomethyl-3-hydroxyoxindole from Rheum maximowiczii Losinsk (Polygonaceae) exhibited activation/inhibition of specific cytokines [5]. 3-Substituted3-hydroxy-2-oxindoles act as synthetic precursors
As an ideal oxidant molecular oxygen has already participated in the construction of a series of structurally diverse skeletons through photocatalysis [34,35,36,37,38,39,40]
Summary
The 3-substituted-3-hydroxy-2-oxindole framework is a privileged motif that is abundant in naturally occurring alkaloids and biologically active products [1,2].
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