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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

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • 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