Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone(R) in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 degrees C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.

Automated summary

A convenient method for preparing nonexplosive cyclic hypervalent iodine(III) oxidants using Oxone(R) in aqueous solution at room temperature has been reported. The obtained 2-iodosobenzoic acids (IBAs) can serve as precursors for other cyclic organoiodine(III) derivatives, providing excellent yields without contamination by hazardous pentavalent iodine(III) compounds.