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

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

Author identifier: 0000-0002-6418-7930

Record's date: 2023-08-05

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: http://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