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]
