Author, as appears in the article.: Franchino, Allegra; Marti, Alex; Nejrotti, Stefano; Echavarren, Antonio M.;
Department: Química Analítica i Química Orgànica
URV's Author/s: ECHAVARREN PABLOS, ANTONIO / Martí Zaragoza, Àlex
Keywords: 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
Abstract: 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.
Thematic Areas: 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
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: antoniomaria.echavarren@urv.cat alex.marti@estudiants.urv.cat
Author identifier: 0000-0002-6418-7930
Record's date: 2024-07-27
Journal volume: 27
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202101751
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Chemistry-A European Journal. 27 (46): 11989-11996
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
Article's DOI: 10.1002/chem.202101751
Entity: Universitat Rovira i Virgili
Journal publication year: 2021
Publication Type: Journal Publications
Repositori URV