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Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
Authors: Burešová Zuzana | Jandová Veronika | Klikar Milan | Grygarová Monika | Bureš Filip
Year: 2022
Type of publication: článek v odborném periodiku
Name of source: Organic and Biomolecular Chemistry
Publisher name: Royal Society of Chemistry
Place: Cambridge
Page from-to: 9378-9384
Titles:
Language Name Abstract Keywords
cze Konstrukce bi(hetero)aromátů pomocí fotochemické cross-couplingové reakce katalyzované dikyanpyrazinem Byla vyvinuta metodika syntézy bi(hetero)aromátů pomocí fotochemické cross-couplingové reakce. Byla vyvinuta metodika syntézy bi(hetero)aromátů pomocí fotochemické cross-couplingové reakce. Reakce byly katalyzovány dikyanpyrazinovým fotoredoxním katalyzátorem, jak odoprovodný mechanismus byla pozorována fotoindukovaná disproporcionace, zejména u derivátů pyrrolu. Vyvinutá metoda umožňuje cross-coupling pětičlenných a šestičlenných (hetero)aromátů jako pyrrol, imidazol, thiazol, oxazol, různé diaziny (pyridin a pyrimidin) a deriváty benzenu. Byl popsán pravděpodobný mechanismus reakce. Bylo připraveno 21 bi(hetero)aromátů ve výtěžcích 19 až 95 %. světlo; aktivace; fotoredoxní katalyzátor; dikyanpyrazin; cross-coupling
eng Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling 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%. light; activation; complexes; radicals

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