344324-66-9

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.