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N-Iodosuccinimide (NIS)

N-Iodosuccinimide (NIS) is an iodinating agent that is used for various electrophilic iodinations and as source for iodine in radical reactions.

Recent Literature

Because of the popularity of coupling reactions, iodoarenes have become increasingly important in organic synthesis. Iodine reacts directly with only the most activated of aromatic substrates which has led to the development of iodonium donating reagents such as NIS¹ and NIS in combination with Triflic acid². More recently it has been discovered that NIS with a catalytic amount of Trifuoroacetic acid will regioselectively iodinate activated aromatic compounds³. Various methoxy- or methyl-substituted aromatic compounds were regioselectively iodinated with N-iodosuccinimide and and a catalytic amount of trifluoroacetic acid with excellent yields under mild conditions and short reaction times⁴.

NIS has been used in combination with Triflic acid² or BF₃-H₂0⁴ to iodinate deactivated arenes. This combination was very effective in iodinating various deactivated aromatics under mild conditions.

Using triethylamine as catalyst in Hunsdiecker reactions with N-Iodosuccinimide as the I⁺ source, cinnamic acids, and propiolic acids are converted to the corresponding α-halostyrenes and 1-halo-1-alkynes in good isolated yields within 1-5 min⁵.
J. Prakash, S. Roy, J. Org. Chem., 2002, 67, 7861-7864.

Various tert-butyldimethylsilyl ethers are easily removed in excellent yields by treatment with a catalytic amount of N-iodosuccinimide in methanol. This method allows a selective deprotection of TBDMS ethers of alcohols in the presence of TBDMS ethers of phenols⁶.
B. Karimi, A. Zamani, D. Zarayee, Tetrahedron Lett., 2004, 45, 9139-9141.

1.Carreno, M. C.; Ruano, J .L .G.; Sanz, G.: Toledo, M. A.; Urbano, A. Tetrahedron Lett. 1996, 37,4081.

2. Olah, G. A.; Qi, W.; Sandford, G;, Prakash, G. K. S. J. Org. Chem. 1993, 58, 3194.

3. Castanet, A.-S.; Colobert, F; P.-E. Broutin, P.-E. Tetrahedron Lett., 2002, 43, 5047-5048.

4. Prakash, G. S.; Mathew, T.; Hoole, D.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. JACS, 2004, 126, 15770-15775.

5. Prakash, J.; Roy, S;  J. Org. Chem., 2002, 67, 7861-7864

6. Karimi, B.; Zamani, A.; Zarayee, D. Tetrahedron Lett., 2004, 45, 9139-9141.

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