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

被引：4

作者：

Vijaykumar, Muniyappa ^{[1
,2
]}

Pradhan, Chandini ^{[1
,2
]}

Gonnade, Rajesh G. ^{[2
,3
]}

Punji, Benudhar ^{[1
,2
]}

机构：

[1] CSIR Natl Chem Lab CSIR NCL, Organ Chem Div, Organometall Synth & Catalysis Lab, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India

[3] CSIR Natl Chem Lab CSIR NCL, Ctr Mat Characterizat, Pune 411008, Maharashtra, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 11期

关键词：

C-H ACETOXYLATION; FUNCTIONALIZATION; ALKYLATION; ACTIVATION; OXINDOLES; DESIGN;

D O I：

10.1021/acs.orglett.3c00342

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1862 / 1867

页数：6

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