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

Drev, Miha (author), Brodnik, Helena (author), Grošelj, Uroš (author), Perdih, Franc (author), Svete, Jurij (author), Štefane, Bogdan (author), Požgan, Franc (author)

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.

• Language: English
• Keywords: ruthenium catalysis, heterocycles, C-H activation, pyridones, 2-bromopyridines
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2024
• Number of pages: 13 str.
• Numbering: Vol. 29, iss. 18, art. 4418
• PID: 20.500.12556/RUL-162191
• UDC: 547.82
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules29184418
• COBISS.SI-ID: 208047363
• Publication date in RUL: 19.09.2024

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: rutenijeva kataliza, heterocikli, C-H aktivacija, piridoni, 2-bromopiridini

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza