Visible‐Light‐Induced C2 Alkylation of Heterocyclic N‐Oxides with N‐Hydroxyphthalimide Esters under Metal‐Free Conditions

A visible‐light‐induced site selective C−H alkylation of heterocyclic N‐oxides with N‐hydroxyphthalimide esters was developed using Eosin Y as the photocatalyst in the presence of Cs2CO3 under redox‐neutral and mild conditions. Using N‐hydroxyphthalimide esters as the radical precursors, quinoline a...

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Veröffentlicht in:	Advanced synthesis & catalysis 2020-11, Vol.362 (21), p.4707-4715
Hauptverfasser:	Qin, Pi‐Tao, Sun, Jing, Wang, Fei, Wang, Jing‐Yun, Wang, He, Zhou, Ming‐Dong
Format:	Artikel
Sprache:	eng
Schlagworte:	Agrochemicals Alkylation Eosin Y Esters Heterocyclic N-oxides NHPI esters Oxides Photocatalysis Quinoline
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creator	Qin, Pi‐Tao Sun, Jing Wang, Fei Wang, Jing‐Yun Wang, He Zhou, Ming‐Dong
description	A visible‐light‐induced site selective C−H alkylation of heterocyclic N‐oxides with N‐hydroxyphthalimide esters was developed using Eosin Y as the photocatalyst in the presence of Cs2CO3 under redox‐neutral and mild conditions. Using N‐hydroxyphthalimide esters as the radical precursors, quinoline and pyridine N‐oxides were readily coupled with a wide range of primary, secondary, and tertiary radicals to afford the desired alkylated heterocyclic N‐oxides in moderated to excellent yields. Importantly, this reaction protocol also successfully demonstrated its applications for the construction of glycosyl or bioactive natural dehydroabietic acid containing heterocyclic N‐oxides, as well as the pharmaceutical and agrochemical active alkylated quinine‐based functional molecules (potential antimalarial drug).
doi_str_mv	10.1002/adsc.202000517
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subjects	Agrochemicals Alkylation Eosin Y Esters Heterocyclic N-oxides NHPI esters Oxides Photocatalysis Quinoline
title	Visible‐Light‐Induced C2 Alkylation of Heterocyclic N‐Oxides with N‐Hydroxyphthalimide Esters under Metal‐Free Conditions
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