Development of Novel Catalytic System, Iodoarene-Oxone^®, on Hypervalent Iodine Oxidation of Phenols and Alcohols

Abstract

Catalytic hypervalent iodine oxidation reactions of phenols and alcohols with iodoarene-Oxone^® system were developed. Oxone^® (2KHSO₅·KHSO₄·K₂SO₄) is well known as a safe and inexpensive oxidant. 4-Iodophenoxyacetic acid (IPAA) is efficient for the phenol oxidations. IPAA is commercially available and it is so soluble with a weak alkaline solution, such as saturated sodium bicarbonate solution, that it is easy separable from the product. 2-Iodobenzamide (IBamide) is efficient for the alcohol oxidations. The oxidation reaction using IBamide with Oxone^® can be carried out at room temperature. The catalytic activity of IBamide is lower than that of 2-iodobenzoic acid at 70 °C, whereas higher at room temperature.