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Pregled bibliografske jedinice broj: 965591

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


Capdevila, Lorena; Andris, Erik; Briš, Anamarija; Tarrés, Màrius; Roldán-Gómez, Steven; Roithová, Jana; Ribas, Xavi
Silver(I)-Catalyzed C–X, C–C, C–N, and C–O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species // ACS Catalysis, 8 (2018), 11; 10430-10436 doi:10.1021/acscatal.8b03257 (međunarodna recenzija, članak, znanstveni)


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

Autori
Capdevila, Lorena ; Andris, Erik ; Briš, Anamarija ; Tarrés, Màrius ; Roldán-Gómez, Steven ; Roithová, Jana ; Ribas, Xavi

Izvornik
ACS Catalysis (2155-5435) 8 (2018), 11; 10430-10436

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Silver ; cross-coupling ; two-electron redox catalysis ; mass spectrometry ; infrared photodissociation spectroscopy

Sažetak
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 L1-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 [5d-Ag(I)-CH3CN], which in solution forms 5a. This work proves that silver can undergo 2-electron redox processes in cross-coupling reactions like Pd and Cu.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove
Institut "Ruđer Bošković", Zagreb

Autor s matičnim brojem:
Anamarija Briš, (317583)

Citiraj ovu publikaciju

Capdevila, Lorena; Andris, Erik; Briš, Anamarija; Tarrés, Màrius; Roldán-Gómez, Steven; Roithová, Jana; Ribas, Xavi
Silver(I)-Catalyzed C–X, C–C, C–N, and C–O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species // ACS Catalysis, 8 (2018), 11; 10430-10436 doi:10.1021/acscatal.8b03257 (međunarodna recenzija, članak, znanstveni)
Capdevila, L., Andris, E., Briš, A., Tarrés, M., Roldán-Gómez, S., Roithová, J. & Ribas, X. (2018) Silver(I)-Catalyzed C–X, C–C, C–N, and C–O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species. ACS Catalysis, 8 (11), 10430-10436 doi:10.1021/acscatal.8b03257.
@article{article, year = {2018}, pages = {10430-10436}, DOI = {10.1021/acscatal.8b03257}, keywords = {silver, cross-coupling, two-electron redox catalysis, mass spectrometry, infrared photodissociation spectroscopy}, journal = {ACS Catalysis}, doi = {10.1021/acscatal.8b03257}, volume = {8}, number = {11}, issn = {2155-5435}, title = {Silver(I)-Catalyzed C–X, C–C, C–N, and C–O Cross-Couplings Using Aminoquinoline Directing Group via Elusive Aryl-Ag(III) Species}, keyword = {silver, cross-coupling, two-electron redox catalysis, mass spectrometry, infrared photodissociation spectroscopy} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
  • Scopus


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