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

K. Surendra, N. Srilakshmi Krishnaveni, M. Arjun Reddy, Y. V. D. Nageswar and K. Rama Rao*

*Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad-500 007, India, Email: ramaraokiict.res.in

K. Surendra, N. Srilakshmi Krishnaveni, M. Arjun Reddy, Y. V. D. Nageswar, K. Rama Rao, J. Org. Chem., 2003, 68, 2058-2059.

DOI: 10.1021/jo026751w


Abstract

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

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Details

The document describes a mild and efficient method for the oxidation of alcohols using o-iodoxybenzoic acid (IBX) catalyzed by β-cyclodextrin (β-CD) in a water/acetone mixture (86:14). This method is environmentally friendly, leveraging the benign nature of water as a solvent and the supramolecular catalysis properties of cyclodextrins. IBX is a hypervalent iodine reagent known for its selective and efficient oxidation capabilities, converting primary and secondary alcohols to aldehydes and ketones, respectively, without overoxidation to acids. The reactions were conducted at room temperature, yielding impressive results (85%-98%) for various alcohols, including those with functional groups like methoxy, nitro, and hydroxy. β-CD was used in catalytic amounts (0.1 mmol per mmol of alcohol), and the reactions did not proceed without it. The process also allows for the recycling of iodosobenzoic acid (IBA) back to IBX and the reuse of β-CD. The methodology is simple, practical, and suitable for commercial applications. The products were characterized using IR, NMR, and mass spectroscopy, and the crude products were purified by column chromatography. This research was supported by CSIR, New Delhi, India, and the findings were published in the Journal of Organic Chemistry in 2003.


Highly Selective Oxidative Cleavage of β-Cyclodextrin-Epoxide/Aziridine Complexes with IBX in Water

K. Surendra, N. S. Krishnaveni, M. A. Reddy, Y. V. D. Nageswar, K. R. Rao, J. Org. Chem., 2003, 68, 9119-9121.


Key Words

IBX, oxidation, hypervalent iodine reagents, ketones, aldehydes, hydroxyketones


ID: J42-Y2003-180