Mild Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX) in Water/Acetone Mixture in the Presence of β-Cyclodextrin

Abstract

A mild and efficient oxidation of alcohols with o-iodoxybenzoic acid (IBX) catalyzed by beta-cyclodextrin in a water/acetone mixture (86:14) has been developed. A series of alcohols were oxidized at room temperature in excellent yields.

Hypervalent Iodine Reagents for the Oxidation of Alcohols and Their Application to Complex Molecule Synthesis

“…Using this system, a series of alcohols are oxidized in water/ acetone (86 : 14) at room temperature in excellent yields. [12] Furthermore, Nicolaou and co-workers reported the one-step synthesis of a,b-unsaturated carbonyl compounds from saturated alcohols and carbonyl compounds by using an excess IBX under heating (60 ± 80 8C), Eq. (7).…”

β-Cyclodextrin coated Fe3O4 nanoparticles: a simple preparation and application for selective oxidation of alcohols in water

“…The formation of aldehydes might be occurred through a SN1 mechanism. Firstly, a β-CD inclusion complex between β-CD and β-Cyclodextrin Coated Fe 3 O 4 Nanoparticles: a Simple Preparation and Application substrate was formed in situ with the help of hydrogen bond, 17 which was dispersed in water as a pseudo homogeneous phase. Carbonium ion was then formed and attacked by ClO -anion on carbon atom.…”

“…The oxidation of alcohols in the presence of β-CD has also been reported. Particular examples were presented with o-iodoxybenzoic acid (IBX), 17 N-bromosuccinimide (NBS), 18,19 NaOCl, 20 as oxidant in water. Despite of the high efficiency of reaction, easy separation and recovery of β-CD, however, still remains a problem.…”

An efficient sonochemical oxidation of benzyl alcohols into benzaldehydes by FeCl3/HNO3 in acetone

“…Representative oxidants for the oxidation of benzyl alcohols to the corresponding benzaldehydes include use of chromium(VI) reagents, [10] transition metal nitrates on solid supports, [11] hypervalent iodine [12], and dimethyl sulfoxides/HBr [13]. In addition Luzzio et al employed a modified Corey-Suggs protocol [14] and Stefan Toma used a heterogeneous mixture of KMnO 4, CuSO 4 Á5H 2 O in dichloromethane [15] for the purpose.…”