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

Hideyasu China; Nami Kageyama; Hotaka Yatabe; Naoko Takenaga; Toshifumi Dohi

doi:10.3390/molecules26071897

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

Molecules. 2021 Mar 27;26(7):1897. doi: 10.3390/molecules26071897.

Authors

Hideyasu China^{1

2}, Nami Kageyama², Hotaka Yatabe², Naoko Takenaga³, Toshifumi Dohi²

Affiliations

¹ Department of Medical Bioscience, Nagahama Institute of Bio-Science and Technology, 1266, Tamuracho Nagahama-shi, Shiga 526-0829, Japan.
² College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga 525-8577, Japan.
³ Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan.

Abstract

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^® 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 °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.

Keywords: Oxone®; cyclic organoiodine(III) compounds; water, solvolytic functionalization, mild condition, metal-free, 2-iodosobenzoic acid.