2-Bromopyridines as Versatile Synthons for Heteroarylated 2-Pyridones via Ru(II)-Mediated Domino C–O/C–N/C–C Bond Formation Reactions
2-Бромопиридины как универсальные синтоны для гетероарилированных 2-пиридонов посредством Ru(II)-опосредованных домино реакций образования связей C–O/C–N/C–C
2024-09-17
SCID: 54.1/xwgpdzt7
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2-bromopyridines2-pyridonesBuchwald–Hartwig-type reactionC–H bond activationRu(II)–KOPiv–Na2CO3 catalytic system
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Abstract (AI)
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–Na2CO3 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.
Key Findings
1
2-Bromopyridines are demonstrated as versatile synthons for constructing multi-heteroarylated 2-pyridone scaffolds under Ru(II)-mediated domino C–O/C–N/C–C bond formation conditions.
2
A Ru(II)–KOPiv–Na2CO3 catalytic system enables synthesis of 2-pyridones bearing 2-pyridyl groups on both nitrogen and carbon from 2-bromopyridines.
3
The reaction sequence likely proceeds via consecutive oxygen incorporation, a Buchwald–Hartwig-type C–N bond-forming step, and C–H bond activation according to preliminary mechanistic studies.
4
Unsubstituted 2-bromopyridine can be converted to a penta-heteroarylated 2-pyridone using the reported method.
Research Object
2-bromopyridines as synthons for the synthesis of multi-heteroarylated 2-pyridones using a Ru(II)–KOPiv–Na2CO3 catalytic system
Research Subject
Development and mechanistic investigation of domino C–O/C–N/C–C bond-forming transformations (including oxygen incorporation, Buchwald–Hartwig-type amination, and C–H activation) that install 2-pyridyl groups on nitrogen and carbon of 2-pyridones
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2024-09-17
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