Palladium‐Catalyzed Photoinduced Regioselective C8 Arylation of 1‐(Pyridin‐2‐yl)quinolin‐4(1 <i>H</i> )‐Ones with Aryl Diazonium Salts

A visible‐light‐mediated regioselective C8 arylation of quinolinones has been developed by merging transition‐metal catalysis with photoredox catalysis. This approach offers broad substrate scope and mild reaction conditions, affording the desired products in up to 85% yield. Furthermore, to investigate the reaction mechanism, several control experiments were performed, including fluorescence quenching studies, quantum yield measurements, light‐on/off experiments, kinetic isotope effect (KIE) analysis, and H/D labeling experiments. This strategy exhibits excellent scalability and also enables subsequent C2 alkenylation.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-11-24
DOI
https://doi.org/10.1002/ejoc.202500961
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Palladium‐Catalyzed Photoinduced Regioselective C8 Arylation of 1‐(Pyridin‐2‐yl)quinolin‐4(1 H )‐Ones with Aryl Diazonium Salts

Rajesh T. Bhawale, Umesh A. Kshirsagar, Biswajit Biswas, Shivaji V. Surve
European Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Palladium‐Catalyzed Photoinduced Regioselective C8 Arylation of 1‐(Pyridin‐2‐yl)quinolin‐4(1 H )‐Ones with Aryl Diazonium Salts

Rajesh T. Bhawale, Umesh A. Kshirsagar, Biswajit Biswas, Shivaji V. Surve
article en

Abstract

A visible‐light‐mediated regioselective C8 arylation of quinolinones has been developed by merging transition‐metal catalysis with photoredox catalysis. This approach offers broad substrate scope and mild reaction conditions, affording the desired products in up to 85% yield. Furthermore, to investigate the reaction mechanism, several control experiments were performed, including fluorescence quenching studies, quantum yield measurements, light‐on/off experiments, kinetic isotope effect (KIE) analysis, and H/D labeling experiments. This strategy exhibits excellent scalability and also enables subsequent C2 alkenylation.

European Journal of Organic ChemistryVol. 29(1)
Indian Institute of Technology Indore (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Council of Scientific and Industrial Research, India, Indian Institute of Technology Indore
Openalex Percentile: Top 73%
Catalytic C–H Functionalization Methods
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