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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

ACS Catalysis

ISSN

2155-5435

e-ISSN

—

Svazek periodika

8

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

10430-10436

Kód UT WoS článku

000449723900057

EID výsledku v databázi Scopus

2-s2.0-85055254433