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Ultrasound-promoted aromatic nucleophilic substitution of dichlorobenzene iron(II) complexes |
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| Authors: | Noureddine Raouafi Khaled Boujlel Christian Amatore Bernd Schöllhorn |
| Institution: | a Département de Chimie, Faculté des Sciences de Tunis, Université de Tunis El Manar, 2092 Tunis, Tunisia b Laboratoire d’Electrochimie, d’Ingénierie Moléculaire et de Catalyse Rédox—LEIMCR, Faculté des Sciences de l’Ingénieur, Université Ferhat ABBAS, DZ-19000 Sétif, Algeria c Département de Chimie, Ecole Normale Supérieure, UMR CNRS 8640 “PASTEUR”, 24 rue Lhomond, 75231 Paris Cedex 05, France |
| Abstract: | The nucleophilic aromatic substitution under ultrasound irradiation of a dichlorobenzene iron η6-complex with various secondary amines is reported. The reaction time at moderate temperatures is considerably shortened (15 min) compared to non sonicated reaction conditions at room temperature (several days) or at solvent refluxing temperature (12-48 h). Controlled mono- or di-substitution was achieved by the tuning of the amine nucleophilicity and the solvent polarity. The method was successfully applied to the synthesis of differently substituted phenylenediamines. |
| Keywords: | Ultrasound Nucleophilic substitution Dihalobenzenes Iron arene complexes Phenylene diamines Anilines |
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