title: Csp2-N bond formation via ligand-free Pd-catalyzed oxidative coupling reaction of N-tosylhydrazones and indole derivatives.
abstract: In a fresh approach to the synthesis of N-vinylazoles, a ligand-free palladium catalytic system was found to promote the Csp(2)-N bond-forming reaction utilizing N-tosylhydrazones and N-H azoles. This process shows functional group tolerance; di-, tri-, and tetrasubstituted N-vinylazoles were obtained in high yields. Under the optimized conditions, the reaction proceeds with high stereoselectivity depending on the nature of the coupling partners.
authors.affiliation: Université Paris-Sud, CNRS, BioCIS-UMR 8076, LabEx LERMIT, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.-B. Clément, Châtenay-Malabry, F-92296, France.
authors.forename: Maxime
authors.initials: M
authors.lastname: Roche
authors.forename: Gilles
authors.initials: G
authors.lastname: Frison
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Olivier
authors.initials: O
authors.lastname: Provot
authors.forename: Abdallah
authors.initials: A
authors.lastname: Hamze
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
mesh_terms: D001393:Azoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011789:Quantum Theory; D014105:Tosyl Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001393:Azoles; D006835:Hydrazones; D007211:Indoles; D008024:Ligands; D014105:Tosyl Compounds; D014753:Vinyl Compounds; D010165:Palladium