Autor según el artículo: Franchino, Allegra; Marti, Alex; Nejrotti, Stefano; Echavarren, Antonio M.;

Departamento: Química Analítica i Química Orgànica

Autor/es de la URV: ECHAVARREN PABLOS, ANTONIO

Palabras clave: Urea Terminal alkynes Tandem cyclization Squaramide Silver compounds Silver additives Silver Quinine Phosphorus compounds Phosphines Phosphine ligands Phosphine derivative Phosphine Oxazoles Metabolism Mesoionic carbenes Ligands Ligand Kinetics Hydrohydrazination Hydrogen bond Hydroamination Gold-mediated cyclization Gold compounds Gold Equilibrium acidities Cycloisomerizations Cyclization Complexes Chlorine compounds Chloride complexes Chloride abstraction Catalyst activity Catalysis Associative mechanisms Additives Addition reactions Activation

Resumen: A library of gold(I) chloride complexes with phosphine ligands incorporating pendant (thio)urea and squaramide H-bond donors was prepared with the aim of promoting chloride abstraction from Au(I) via H-bonding. In the absence of silver additives, complexes bearing squaramides and trifluoromethylated aromatic ureas displayed good catalytic activity in the cyclization of N-propargyl benzamides, as well as in a 1,6-enyne cycloisomerization, a tandem cyclization-indole addition reaction and the hydrohydrazination of phenylacetylene. Kinetic studies and DFT calculations indicate that the energetic span of the reaction is accounted by both the chloride abstraction step, facilitated by the bidentate H-bond donor via an associative mechanism, and the subsequent cyclization step.

Áreas temáticas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física

Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/

Direcció de correo del autor: antoniomaria.echavarren@urv.cat

Identificador del autor: 0000-0002-6418-7930

Fecha de alta del registro: 2023-08-05

Volumen de revista: 27

Versión del articulo depositado: info:eu-repo/semantics/publishedVersion

Enlace a la fuente original: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202101751

URL Documento de licencia: http://repositori.urv.cat/ca/proteccio-de-dades/

Referencia al articulo segun fuente origial: Chemistry-A European Journal. 27 (46): 11989-11996

Referencia de l'ítem segons les normes APA: Franchino, Allegra; Marti, Alex; Nejrotti, Stefano; Echavarren, Antonio M.; (2021). Silver-Free Au(I) Catalysis Enabled by Bifunctional Urea- and Squaramide-Phosphine Ligands via H-Bonding. Chemistry-A European Journal, 27(46), 11989-11996. DOI: 10.1002/chem.202101751

DOI del artículo: 10.1002/chem.202101751

Entidad: Universitat Rovira i Virgili

Año de publicación de la revista: 2021

Tipo de publicación: Journal Publications