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
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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
—
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
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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