Thiolate Bridged Gold(I)–NHC Catalysts: New Approach for Catalyst Design and its Application to Trapping Catalytic Intermediates

Visbal, R. ; Herrera, R. P. (Universidad de Zaragoza) ; Gimeno, M. C. (Universidad de Zaragoza)

Resumen: New dinuclear N-heterocyclic gold complexes with bridging thiolate ligands have been designed as catalytic precursors with desired properties such as stability, recyclability and that do not require additives. The dinuclear compound [(AuNHC)2(µ-SC6F5)]OTf could slowly release the active catalytic species [Au(NHC)]+ and the precursor [Au(SC6F5)(NHC)] in solution, which means that both species would remain stable throughout the catalytic cycle and the pre-catalyst could easily be recovered. The properties exhibited by the complexes have been taken advantage of to gain new insights on the gold-catalyzed hydroalkoxylation of alkynes, with the aim of clarifying all the steps of the catalytic cycle, together with the characterization of intermediates and final products. Isolation and characterization of the pure final spiroketals and the thermodynamic intermediate have been achieved for the first time. Moreover, the kinetic intermediate has also been detected for the first time.

Idioma: Inglés

DOI: 10.1002/chem.201903494

Año: 2019

Publicado en: Chemistry - A European Journal 25, 69 (2019), 15837-15845
ISSN: 0947-6539

Factor impacto JCR: 4.857 (2019)

Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 44 / 176 = 0.25 (2019) - Q1 - T1

Factor impacto SCIMAGO: 1.681 - Catalysis (Q1) - Organic Chemistry (Q1) - Chemistry (miscellaneous) (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E07-17R
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2016-75816-C2-1-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P

Tipo y forma: Artículo (PostPrint)

Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)