Catalytic photoredox C–H arylation of 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium tetrafluoroborates and related heteroaryl diazonium salts

Antolinc, Kris (author), Brodnik Žugelj, Helena (author), Grošelj, Uroš (author), Štefane, Bogdan (author), Petek, Nejc (author), Svete, Jurij (author)

Irradiation of mixtures of title diazonium salts and heteroarenes with green light (510 nm) in the presence of eosin Y disodium salt (EY-Na$_2$) as a photocatalyst furnished the corresponding arylation products in 8−63% yields. The proposed photocatalytic cycle is analogous to that proposed previously for closely related photoredox C−H arylations with aryl diazonium salts as aryl radical sources. This method has a broad substrate scope and represents a metal-free alternative for the synthesis of 3-heteroaryl-substituted 4H-quinolizin-4-ones and azino- and azolo-fused pyrimidones with a bridgehead nitrogen atom.

• Language: English
• Keywords: quinolizines, pyrido[1, 2-a]pyrimidines, thiazolo[3, 2-a]pyrimidines, photoredox catalysis, arylation, cross-coupling, chemical reactions, mixtures, molecular structure, salts
• 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: 2023
• Number of pages: Str. 13934−13945
• Numbering: Vol. 88, iss. 19
• PID: 20.500.12556/RUL-152684
• UDC: 547.85-304.4
• ISSN on article: 0022-3263
• DOI: 10.1021/acs.joc.3c01517
• COBISS.SI-ID: 163747843
• Publication date in RUL: 04.12.2023

Record is a part of a journal

• Title: Journal of organic chemistry
• Shortened title: J. org. chem.
• Publisher: American Chemical Society
• ISSN: 0022-3263
• COBISS.SI-ID: 235287

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: kinolizini, pirido[1, 2-a]pirimidini, tiazolo[3, 2-a]pirimidini, fotoredoks kataliza, arilacija, spajanje

Projects

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