Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F22%3A39919108" target="_blank" >RIV/00216275:25310/22:39919108 - isvavai.cz</a>
Výsledek na webu
<a href="https://pubs.rsc.org/en/content/articlelanding/2022/OB/D2OB01836E" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2022/OB/D2OB01836E</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d2ob01836e" target="_blank" >10.1039/d2ob01836e</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
Popis výsledku v původním jazyce
A photochemical cross-coupling protocol towards bi(hetero)aryls has been developed. The coupling reactions were mediated by dicyanopyrazine photoredox catalyst, while a photoinduced disproportionation process has been identified as an accompanying mechanism, especially for pyrrole derivatives. The developed method allows the cross-coupling of five-membered rings such as pyrrole, imidazole, thiazole and oxazole as well as various diazines (pyridine and pyrimidine) and benzene derivatives. A plausible mechanism of the reaction has also been disclosed. The practical application and relevance of the developed method were demonstrated by constructing an atorvastatin core or by the gradual functionalization of benzo[c][1,2,5]thiadiazole. In total, twenty-one bi(hetero)aryls were prepared in yields ranging from 19 to 95%.
Název v anglickém jazyce
Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
Popis výsledku anglicky
A photochemical cross-coupling protocol towards bi(hetero)aryls has been developed. The coupling reactions were mediated by dicyanopyrazine photoredox catalyst, while a photoinduced disproportionation process has been identified as an accompanying mechanism, especially for pyrrole derivatives. The developed method allows the cross-coupling of five-membered rings such as pyrrole, imidazole, thiazole and oxazole as well as various diazines (pyridine and pyrimidine) and benzene derivatives. A plausible mechanism of the reaction has also been disclosed. The practical application and relevance of the developed method were demonstrated by constructing an atorvastatin core or by the gradual functionalization of benzo[c][1,2,5]thiadiazole. In total, twenty-one bi(hetero)aryls were prepared in yields ranging from 19 to 95%.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
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)
Ostatní
Rok uplatnění
2022
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Organic and Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
1477-0539
Svazek periodika
20
Číslo periodika v rámci svazku
47
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
7
Strana od-do
9378-9384
Kód UT WoS článku
000885698100001
EID výsledku v databázi Scopus
2-s2.0-85142412314