2-Bromopyridines as versatile synthons for heteroarylated 2-pyridones via Ru(II)-mediated domino C–O/C–N/C–C bond formation reactions

A novel methodology for the synthesis of 2-pyridones bearing a 2-pyridyl group on nitrogen and carbon atoms, starting from 2-bromopyridines, was developed employing a simple Ru(II)–KOPiv–Na$_2$CO$_3$ catalytic system. Unsubstituted 2-bromopyridine was successfully converted to the penta-heteroarylated 2-pyridone product using this method. Preliminary mechanistic studies revealed a possible synthetic pathway leading to the multi-heteroarylated 2-pyridone products, involving consecutive oxygen incorporation, a Buchwald–Hartwig-type reaction, and C–H bond activation.

Publication Details

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Repository of the University of Ljubljana (University of Ljubljana)
Published
2024-09-19
Primary Topic
Catalytic C–H Functionalization Methods
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article
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article

2-Bromopyridines as versatile synthons for heteroarylated 2-pyridones via Ru(II)-mediated domino C–O/C–N/C–C bond formation reactions

Repository of the University of Ljubljana (University of Ljubljana)
Catalytic C–H Functionalization Methods
article

2-Bromopyridines as versatile synthons for heteroarylated 2-pyridones via Ru(II)-mediated domino C–O/C–N/C–C bond formation reactions

article en

Abstract

A novel methodology for the synthesis of 2-pyridones bearing a 2-pyridyl group on nitrogen and carbon atoms, starting from 2-bromopyridines, was developed employing a simple Ru(II)–KOPiv–Na$_2$CO$_3$ catalytic system. Unsubstituted 2-bromopyridine was successfully converted to the penta-heteroarylated 2-pyridone product using this method. Preliminary mechanistic studies revealed a possible synthetic pathway leading to the multi-heteroarylated 2-pyridone products, involving consecutive oxygen incorporation, a Buchwald–Hartwig-type reaction, and C–H bond activation.

Repository of the University of Ljubljana (University of Ljubljana)
Javna Agencija za Raziskovalno Dejavnost RS
Openalex Percentile: Top 56%
Catalytic C–H Functionalization Methods
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2-Bromopyridines as versatile synthons for heteroarylated 2-pyridones via Ru(II)-mediated domino C–O/C–N/C–C bond formation reactions · Repository of the University of Ljubljana (University of Ljubljana) (2024) | TGRS Research Map | TGRS