Facile, One-Pot, and Gram-Scale Synthesis of 3,4,5-Triiodoanisole through a C-H Iodination/ipso-Iododecarboxylation Strategy: Potential Application towards 3,4,5-Trisubstituted Anisoles

A facile, efficient, and gram‐scale method for the conversion of para‐anisic acid into 3,4,5‐triiodoanisole through a one‐pot C–H iodination/ipso‐iododecarboxylation reaction was investigated. Commercially available benzoic acid was used, which allowed the reaction to be performed on a multigram scale in good yield. This report discloses a practical method for the one‐pot synthesis of hitherto unknown 3,4,5‐triiodoanisole that is catalytic, scalable, efficient, and easy to work up and purify. Potential application of the target compound as a precursor for novel site‐selective metal–iodine exchange and Suzuki–Miyaura cross‐coupling reactions were also explored. 3,4,5‐Trisubstituted anisole derivatives were provided in a highly regioselective fashion; these compounds are useful building blocks in synthesis and indeed are hard to prepare by any other means. The facile and efficient synthesis of hitherto unknown 3,4,5‐triiodoanisole in a tandem one‐pot C–H iodination/ipso‐iododecarboxylation reaction that is catalytic, scalable, easy to work up, and easy to purify is disclosed. Potential application of the target compound as a precursor for novel site‐selective metal–iodine exchange and Suzuki–Miyaura cross‐coupling reactions are demonstrated.