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

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• 作者：Noureddine Raouafi ; Nadra Belhadj ; Khaled Boujlel ; Ali Ourari ; Christian Amatore ; Emmanuel Maisonhaute ; Bernd Schö ; llhorn
• 关键词：Ultrasound ; Nucleophilic substitution ; Dihalobenzenes ; Iron arene complexes ; Phenylene diamines ; Anilines
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：15 April 2009
• 年：2009
• 卷：50
• 期：15
• 页码：1720-1722
• 全文大小：187 K

文摘

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.