A mild and regioselective method for direct halogenation of activated arenas has been developed. The transformation uses iron(III) nitrate nonahydrate as catalyst for the nucleophilic aromatic substitution by TMSCl or TMSBr and apply to arenes bearing one or multiple electron donating groups. The reaction established direct arene halogenation featuring ancillary-ligand-free catalysis with inexpensive iron salts as the catalyst. The facile nature of this reaction allows one-pot, highly para-selective formation of carbon-halogen bonds in mild conditions. The nucleophilic aromatic substitution mechanism sheds new light on aromatic halogenation, which traditionally employs electrophilic aromatic substitution approach. The resulting para-halogenated aryl compounds are utilized as key building blocks for the synthesis of natural products and bioactive molecules due to the versatility of halogen in numerous functional group interconversions.

Iron(III)-catalyzed nucleophilic arene halogenation

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