N-Iodosuccinimide (NIS)

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]

References and Notes

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• 11 Sniady A. Wheeler KA. Dembinski R. Org. Lett.  2005,  7:  1769 
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• 14 Thiebes C. Prakash GKS. Petasis NA. Olah GA. Synlett  1998,  141 
• 15 Dewanjee MK. Radioiodination: Theory, Practice, and Biological Applications   Kluwer Academic Publishers; Boston: 1992.  p.115 
• 16 Paolini L. Petricci E. Corelli F. Botta M. Synthesis  2003,  1039 
• 17 Singletary JA. Lam H. Dudley GB. J. Org. Chem.  2005,  70:  739 
• 18 Hofmeister H. Annen K. Laurent H. Wiechert R. Angew. Chem., Int. Ed. Engl.  1984,  23:  727 
• 19 Amatore C. Blart E. Genet JP. Jutand A. Lemaire-Audoire S. Savignac M. J. Org. Chem.  1995,  60:  6829 
• 20a Yao T. Zhang X. Larock RC. J. Org. Chem.  2005,  70:  7679 
• 20b Colobert F. Castanet A.-S. Abillard O. Eur. J. Org. Chem.  2005,  3334 
• 21 Ma S. Lu L. J. Org. Chem.  2005,  70:  7629