Towards the Synthesis of Substituted o-Iodoxybenzoic Acid (IBX)

摘要

o-iodoxybenzoic acid (IBX) 48 is an effective and a mild oxidant reagent belong to the heterocyclic compounds of pentavalent iodine family. It has been reported that IBX 48 has the ability to oxidize alcohols selectively to the corresponding carbonyl compounds or some other important transformations. However, IBX suffers from several drawbacks including limited solubility in most common organic solvents and its potential explosive nature when synthesized using the initially reported KBrO3 protocol. In few past years, our research group was able to synthesis IBX derivatives that are soluble in most eco-friendly solvent at all, water. For this current project we aimed to modify the substitution pattern on the arenes ring to enhance the solubility of the IBX derivatives. We decided that appending amide functionality on to the ring would be a worthwhile target to synthesis. The structures of the decided derivatives are 100 and 108. However, the time limitation has prevented us to achieve the final goal however several important derivatives and precursors of 98 and 107 have been synthesized and are reported herein.