Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
Original language description
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%.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA22-14988S" target="_blank" >GA22-14988S: DicyanoPyraZine: Versatile Tool for Photoredox Catalysis</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic and Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
1477-0539
Volume of the periodical
20
Issue of the periodical within the volume
47
Country of publishing house
GB - UNITED KINGDOM
Number of pages
7
Pages from-to
9378-9384
UT code for WoS article
000885698100001
EID of the result in the Scopus database
2-s2.0-85142412314