Ultrasound-promoted aromatic nucleophilic substitution of dichlorobenzene iron(II) complexes

✍ Scribed by Noureddine Raouafi; Nadra Belhadj; Khaled Boujlel; Ali Ourari; Christian Amatore; Emmanuel Maisonhaute; Bernd Schöllhorn

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 187 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.01.128

✦ Synopsis

The nucleophilic aromatic substitution under ultrasound irradiation of a dichlorobenzene iron g 6 -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.