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Silver(I)-Catalyzed C-X, C-C, C-N, and C-O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10384670" target="_blank" >RIV/00216208:11310/18:10384670 - isvavai.cz</a>

  • Result on the web

    <a href="https://doi.org/10.1021/acscatal.8b03257" target="_blank" >https://doi.org/10.1021/acscatal.8b03257</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1021/acscatal.8b03257" target="_blank" >10.1021/acscatal.8b03257</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Silver(I)-Catalyzed C-X, C-C, C-N, and C-O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species

  • Original language description

    Cross-coupling transformations are a powerful tool in organic synthesis. It is known that this kind of transformation undergoes 2-electron redox processes, and, for this reason, silver has been nearly forgotten as catalyst for cross couplings because silver is mainly considered as a 1-electron redox metal. Herein, we disclose effective Ag(I)-catalyzed cross coupling transformations using bidentate aminoquinoline as a directing group toward different nucleophiles to form C-C, C-N, and C-O bonds. DFT calculations indicate the feasible oxidative addition of L-I-I substrate via the Ag(I)/Ag(III) catalytic cycle. Furthermore, ion spectroscopy experiments suggest a highly reactive aryl-Ag(III) that in the absence of nucleophiles reacts to form an intermolecular cyclic product [Sd-Ag(I)-CH3CN], which in solution forms Sa. This work proves that silver can undergo 2-electron redox processes in cross-coupling reactions like Pd and Cu.

  • 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

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2018

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    ACS Catalysis

  • ISSN

    2155-5435

  • e-ISSN

  • Volume of the periodical

    8

  • Issue of the periodical within the volume

    11

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    7

  • Pages from-to

    10430-10436

  • UT code for WoS article

    000449723900057

  • EID of the result in the Scopus database

    2-s2.0-85055254433