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Synlett 2006(20): 3550-3551  
DOI: 10.1055/s-2006-956469
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© Georg Thieme Verlag Stuttgart · New York

Sodium Periodate (NaIO4) -A Versatile Reagent in Organic Synthesis

Majid Rezaeivalla*
Faculty of Chemistry, Bu-Ali Sina University, Hamadan 6517838683, Iran
e-Mail: mrezaeivala@gmail.com;
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Publication History

Publication Date:
08 December 2006 (online)

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Introduction

Sodium periodate (sodium metaperiodate), NaIO4 (mp 300 °C; Figure 1), is commercially available and is applied mainly in aqueous or aqueous-alcoholic solutions. Like the free periodic acid, sodium periodate cleaves ­vicinal diols to carbonyl compounds. [1] The popularity stems from its specificity, its reactivity under neutral and mild ­conditions which is compatible with a wide range of functionalities, its stability, and its low cost. [2] Sulfides are transformed by sodium periodate into sulfoxides. It is also a reoxidant of lower-valency ruthenium in oxidations with ruthenium tetroxide. [3]

Figure 1

Tetrabutylammonium periodate, (n-Bu)4NIO4 (mp 175 °C), which is usually prepared in situ from tetrabutyl­ammonium hydrogen sulfate and sodium periodate, [4] is useful in two-phase systems, because it dissolves in ­chloroform and other organic solvents. [3] It is used in ­homogeneous oxidations of sulfides, 2-hydroxy acids, and α-bromoketones. [5]