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

[Image: see text] 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...

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Autores principales: Antolinc, Kris, Brodnik, Helena, Grošelj, Uroš, Štefane, Bogdan, Petek, Nejc, Svete, Jurij
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563132/
https://www.ncbi.nlm.nih.gov/pubmed/37676813
http://dx.doi.org/10.1021/acs.joc.3c01517
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author Antolinc, Kris
Brodnik, Helena
Grošelj, Uroš
Štefane, Bogdan
Petek, Nejc
Svete, Jurij
author_facet Antolinc, Kris
Brodnik, Helena
Grošelj, Uroš
Štefane, Bogdan
Petek, Nejc
Svete, Jurij
author_sort Antolinc, Kris
collection PubMed
description [Image: see text] 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.
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spelling pubmed-105631322023-10-11 Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts Antolinc, Kris Brodnik, Helena Grošelj, Uroš Štefane, Bogdan Petek, Nejc Svete, Jurij J Org Chem [Image: see text] 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. American Chemical Society 2023-09-07 /pmc/articles/PMC10563132/ /pubmed/37676813 http://dx.doi.org/10.1021/acs.joc.3c01517 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Antolinc, Kris
Brodnik, Helena
Grošelj, Uroš
Štefane, Bogdan
Petek, Nejc
Svete, Jurij
Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
title Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
title_full Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
title_fullStr Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
title_full_unstemmed Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
title_short Catalytic Photoredox C–H Arylation of 4-Oxo-4H-pyrido[1,2-a]pyrimidine-3-diazonium Tetrafluoroborates and Related Heteroaryl Diazonium Salts
title_sort catalytic photoredox c–h arylation of 4-oxo-4h-pyrido[1,2-a]pyrimidine-3-diazonium tetrafluoroborates and related heteroaryl diazonium salts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10563132/
https://www.ncbi.nlm.nih.gov/pubmed/37676813
http://dx.doi.org/10.1021/acs.joc.3c01517
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