Catalytic Photoredox C-H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts

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 4Hquinolizin-4-ones and azino-and azolo-fused pyrimidones with a bridgehead nitrogen atom.

Automated summary

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 furnishes the corresponding arylation products in 8-63% yields. This method has a broad substrate scope and serves as a metal-free alternative for the synthesis of 3-heteroaryl-substituted 4Hquinolizin-4-ones and azino-and azolo-fused pyrimidones with a bridgehead nitrogen atom.