title: Synthesis of ortho/ortho'-substituted 1,1-diarylethylenes through cross-coupling reactions of sterically encumbered hydrazones and aryl halides.
abstract: The reactivity of sterically hindered N-tosylhydrazones 2 featuring ortho/ortho'-substituents on the aromatic ring with various ortho-, meta-, and para-substituted aryl halides 3 was investigated. To accomplish successfully this challenging coupling, fine-tuning of the reaction conditions were required. The newly established PdCl(2)(MeCN)(2)/Xphos/NaO-t-Bu/F-benzene system in a sealed tube is compatible with a broad spectrum of both coupling partners, regardless of their electronic and steric nature. This protocol has been applied successfully to the synthesis of a xanthene derivative.
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: Abdallah
authors.initials: A
authors.lastname: Hamze
authors.forename: Olivier
authors.initials: O
authors.lastname: Provot
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Mouad
authors.initials: M
authors.lastname: Alami
mesh_terms: D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D005030:Ethylenes / Q000138:chemical synthesis* / Q000737:chemistry*; D006835:Hydrazones / Q000138:chemical synthesis* / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003432:Cross-Linking Reagents; D005030:Ethylenes; D006835:Hydrazones; D006846:Hydrocarbons, Halogenated; D014966:Xanthenes