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.
Towards 3,4,5-Trisubstituted Anisoles. -The reaction can be performed on a multigram scale in good yield and is catalytic, scalable, and efficient with simple work-up and purification processes. Potential application of the target compound as a precursor for novel site-selective metal-iodine exchange and Suzuki-Miyaura cross-coupling reactions are also explored. 3,4,5-Trisubstituted anisole derivatives are obtained with high regioselectivity. -(AL-ZOUBI*, R. M.; AL-MUGHAID, H.; AL-ZOUBI, M. A.; JARADAT, K. T.; MCDONALD, R.; Eur. J. Org. Chem. 2015, 25, 5501-5508, http://dx.
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