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Synlett 2006(6): 960-961  
DOI: 10.1055/s-2006-939055
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

N-Iodosuccinimide (NIS)

Adam Sniady*
Department of Chemistry, Oakland University, Rochester, MI 48309-4477, USA
e-Mail: aksniady@oakland.edu;
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Publication History

Publication Date:
14 March 2006 (online)

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Introduction

N-Iodosuccinimide (NIS) is a well-known iodination ­reagent that has found many applications in organic synthesis since it was first reported by Bunge. [1] [2] It is a colorless, stable solid, commercially available, and is widely used in organic transformations. It can be applied for ­iodination of arenes, [3] [4] halodecarboxylation, [5] [6] iodolysis of the Si-C bond, [7] [8] and chemoselective cleavage of silyl ethers. [9] Recent reports employ NIS in ring-opening reactions [10] or electrophilic cyclizations to yield substi­tuted furans [11] and isoxazolidines. [12] Some of the examples ­reported in this article have roots in earlier reactions that have already been reviewed. [13]

One way to prepare NIS is to combine N-silversuccin­imide and molecular iodine. The reaction is carried out in dioxane, since in acetone the formation of a lachrymatory side-product was observed. [2] NIS can also be generated in situ from sodium iodide and N-chlorosuccinimide in ­acetonitrile. [14] The use of Na125I in the last process leads to isotopically labelled NIS, rendering the reagent useful in medical sciences for the preparation of radiolabelled ­diagnostic or therapeutic agents. [15]