title: Metal-Free Synthesis of N-Aryl Amides using Organocatalytic Ring-Opening Aminolysis of Lactones.
abstract: Catalytic ring-opening of bio-sourced non-strained lactones with aromatic amines can offer a straightforward, 100 % atom-economical, and sustainable pathway towards relevant N-aryl amide scaffolds. Herein, the first general, metal-free, and highly efficient N-aryl amide formation is reported from poorly reactive aromatic amines and non-strained lactones under mild operating conditions using an organic bicyclic guanidine catalyst. This protocol has high application potential as exemplified by the formal syntheses of drug-relevant molecules.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Wusheng
authors.initials: W
authors.lastname: Guo
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: José Enrique
authors.initials: JE
authors.lastname: Gómez
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Luis
authors.initials: L
authors.lastname: Martínez-Rodríguez
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.|Centro de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016, Lisboa, Portugal.|Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisboa, Portugal.
authors.forename: Nuno A G
authors.initials: NAG
authors.lastname: Bandeira
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.|Departament de Química Física i Inorgánica, Universitat Rovira i Virgili, Marcel⋅lí Domingo s/n, 43007, Tarragona, Spain.
authors.forename: Carles
authors.initials: C
authors.lastname: Bo
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.|Catalan Institute for Research and Advanced Studies (ICREA), Pg. Lluis Companys 23, 08010, Barcelona, Spain.
authors.forename: Arjan W
authors.identifier: 0000-0002-7402-4764
authors.initials: AW
authors.lastname: Kleij
mesh_terms: D000577:Amides / Q000138:chemical synthesis; D000588:Amines; D002384:Catalysis; D019791:Guanidine; D007783:Lactones / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D007783:Lactones; D019791:Guanidine
keywords: N-aryl amides; aromatic amines; lactones; organocatalysis; ring-opening aminolysis