Iodic Acid (HIO3)

Arash Ghorbani Choghamarani

doi:10.1055/s-2006-949618

Synlett 2006(14): 2347-2348
DOI: 10.1055/s-2006-949618

SPOTLIGHT

Iodic Acid (HIO₃)

Arash Ghorbani Choghamarani*^a,b
^a Chemistry Department, Faculty of Science, Bu-Ali Sina University, Hamadan, Iran
^b Chemistry Building, The University of Western Ontario, London, ON N6A 5B7, Canada
e-Mail: a-ghorbani@basu.ac.ir; e-Mail: aghorban@uwo.ca;

Abstract

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Biographical Sketches

Arash Ghorbani Choghamarani was born in Kermanshah, Iran in 1979. He finished his undergraduate studies in applied chemistry at Bu-Ali Sina University of Hamadan (2001) and received his M.Sc. in organic chemistry under the supervision of Prof. Mohammad Ali Zolfigol^a (2003) and subsequently began his Ph.D. studies in organic chemistry with the same supervisor. At present, he is working as a visiting graduate student under the supervision of Professor Robert H. E. Hudson^b at the University of Western Ontario, London, Ontario, Canada (since September 2005).His research interests focus on the application of new reagents in organic reactions, the synthesis of organic compounds and some bicyclic fluorescent nucleosides.

Introduction

Iodic acid (HIO₃) has attracted much interest owing to its potential as oxidant, [1-8] reagent [9-12] and acidic source. [13] [14] The use of iodic acid has been known for a long time and has been widely employed in numerous and different organic reactions such as: oxidation of sulfides, [1] [3] iodination, [10] [12] deprotection, [13] nitrosation, [14] and dehydrogenation of aldehydes and ketones. [15] This reagent has several advantages: cost-effectiveness, non-toxicity, easy and clean workup of products.

Abstracts


(A) Patil et al. reported a useful method for the iodination of hydroxy aryl ketones; they showed a variety of ortho-hydroxy-substituted aromatic carbonyl compounds which were selectively iodinated in 81-87% yield by using iodine and iodic acid. [10]
(B) Zolfigol and co-workers have used HIO₃ and NaNO₂ in the presence of wet SiO₂ as a nitrosating agent for the effective and selective nitrosation of secondary amines under mild and heterogeneous conditions in good yields. [14]
(C) Shirini et al. reported a simple and efficient method for the oxidation of thiols to disulfides and sulfides to sulfoxides in 87-95% yield using aqueous HIO₃ at room temperature. [3] Also Lakouraj and co-workers have explained the utility of HIO₃ for oxidation of sulfides to sulfoxides in the presence of wet SiO₂ under solvent-free conditions. [1]
(D) Ketoximes and aromatic aldoximes are converted to the corresponding carbonyl compounds with HIO₃ under mild and heterogeneous conditions in CH₂Cl₂ at room temperature in 67-97% yields. [4] Also deoximation and dehydrazonation have been reported using HIO₃ in the presence of wet SiO₂ under solvent-free conditions. [16]
(E) A variety of aldehydes and ketones were readily and selectively transformed to 1,3-saturated aldehydes and ketones with HIO₃ and I₂O₅ at 45-65 °C in good yields. [15]
(F) Hashemi and Akhbari showed the conversion of a variety of aromatic amines into their corresponding quinines under microwave irradiation. [8]
(G) A variety of thioacetals and thioketals were deprotected to the corresponding carbonyl compounds with HIO₃ in the presence of wet SiO₂ at room temperature under solvent-free conditions. [13]