Acid-activated hypervalent iodine(III) reagents are useful oxidants, which can be used for various synthetically useful oxidative transformations. Several activated iodine(III) reagents (Koser reagent, and ArIO-18C6 complex derivatives) are stable, isolable compounds, and can be used at room temperature. However, most of them cannot be isolated and characterized because they are air sensitive, and hydroscopic compounds. Recently, the more stable <i>ortho</i>-substituted pseudocyclic iodine(III) reagents with intramolecular secondary bonding have been developed. Herein, we disclose the preparation, structural investigation, and versatile reactivity of the novel stable acid-activated pseudocyclic iodine(III) reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]-iodobenzoic acid (IBA–OTf), which is the first example of stable activated hydroxy(aryiodonium) triflate species generated from 2-iodosylbenzoic acid (IBA) and trifluoromethanesulfonic acid. This novel reagent showed the high reactivity and could be also used for various oxidative transformations.

Preparation and reactivity of activated IBA-OTf reagent

251st National Meeting (2016)

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