Divergent photoreduction of nitroaromatic compounds catalysed by dithienoquinoxaline

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F25%3A39923128" target="_blank" >RIV/00216275:25310/25:39923128 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/25:43932040

Výsledek na webu

<a href="https://doi.org/10.1016/j.jcat.2025.116033" target="_blank" >https://doi.org/10.1016/j.jcat.2025.116033</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.jcat.2025.116033" target="_blank" >10.1016/j.jcat.2025.116033</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Divergent photoreduction of nitroaromatic compounds catalysed by dithienoquinoxaline

Popis výsledku v původním jazyce

Nitroaromatic compounds can be conveniently reduced to anilines with the aid of a variety of chemical reductants. However, chemodivergent and chemoselective reduction of functionalized nitroaromatics into valuable nitroso, azo(xy), (hydr)azo and (hydroxyl)amino derivatives remains rather elusive. Electro- and photochemical strategies utilizing various catalytic systems and reaction media have been tested but most have been directed towards individual reduction products. Here, we present the photoredox-enabled chemodivergent reduction of nitroaromatics to nitroso, bis-(N,O-diacetyl)-N-arylhydroxylamine, azoxy, azo and amino derivatives. The developed protocol utilizes a novel photocatalyst, 6,9-dimethoxydithieno[2,3-f:3 &apos;,2 &apos;-h]quinoxaline-2,3-dicarbonitrile, and Hantzsch ester/triethanolamine as reductants. With the single organic photocatalyst, the reaction environment, temperature, time and catalyst loading can be varied to achieve chemodivergent photoreduction of nitroaromatics bearing various functional groups and to access a library of valuable products. The application of this methodology to multigram preparations of molecules of pharmaceutical and industrial relevance highlights its practical utility.

Název v anglickém jazyce

Divergent photoreduction of nitroaromatic compounds catalysed by dithienoquinoxaline

Popis výsledku anglicky

Nitroaromatic compounds can be conveniently reduced to anilines with the aid of a variety of chemical reductants. However, chemodivergent and chemoselective reduction of functionalized nitroaromatics into valuable nitroso, azo(xy), (hydr)azo and (hydroxyl)amino derivatives remains rather elusive. Electro- and photochemical strategies utilizing various catalytic systems and reaction media have been tested but most have been directed towards individual reduction products. Here, we present the photoredox-enabled chemodivergent reduction of nitroaromatics to nitroso, bis-(N,O-diacetyl)-N-arylhydroxylamine, azoxy, azo and amino derivatives. The developed protocol utilizes a novel photocatalyst, 6,9-dimethoxydithieno[2,3-f:3 &apos;,2 &apos;-h]quinoxaline-2,3-dicarbonitrile, and Hantzsch ester/triethanolamine as reductants. With the single organic photocatalyst, the reaction environment, temperature, time and catalyst loading can be varied to achieve chemodivergent photoreduction of nitroaromatics bearing various functional groups and to access a library of valuable products. The application of this methodology to multigram preparations of molecules of pharmaceutical and industrial relevance highlights its practical utility.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA22-14988S" target="_blank" >GA22-14988S: DikyanPyraZin: Všestranný nástroj fotoredoxní katalýzy</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Catalysis

ISSN

0021-9517

e-ISSN

1090-2694

Svazek periodika

445

Číslo periodika v rámci svazku

May 2025

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

9

Strana od-do

116033

Kód UT WoS článku

001432138300001

EID výsledku v databázi Scopus

2-s2.0-85218355732