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. 2023 Mar 24;25(11):1862-1867.
doi: 10.1021/acs.orglett.3c00342. Epub 2023 Mar 15.

Palladium-Catalyzed Chemoselective Oxygenation of C(sp2)-H and C(sp3)-H Bonds in Isatins

Muniyappa Vijaykumar  1 , Chandini Pradhan  1 , Rajesh G Gonnade  1 , Benudhar Punji  1
Affiliations

Palladium-Catalyzed Chemoselective Oxygenation of C(sp2)-H and C(sp3)-H Bonds in Isatins

Muniyappa Vijaykumar et al. Org Lett. .

Abstract

The palladium-catalyzed chemoselective C(sp2)-H and C(sp3)-H bond oxygenation of substituted isatin derivatives is reported. This mild protocol exhibits the C5 C(sp2)-H oxygenation of isatins through electrophilic intermolecular C-H palladation in concentrated solutions using PhI(OAc)2 or Selectfluor as an oxidant, whereas it exhibits-N-CH3 C(sp3)-H oxygenation in dilute solutions via carbonyl-assisted intramolecular palladation in the presence of K2S2O8. This oxygenation reaction provides a direct and unified approach for synthesizing diverse oxygenated isatins with sensitive functionalities, including biorelevant compounds.

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