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
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 times.
A.-S. Castanet, F. Colobert, P.-E. Broutin, Tetrahedron Lett., 2002,
43, 5047-5048.
N-Halosuccinimides are efficiently activated in
trifluoromethanesulfonic acid and BF3-H2O, allowing
the halogenations of deactivated aromatics. BF3-H2O is
more economic, easy to prepare, nonoxidizing, and offers sufficiently high
acidity.
G. K. S. Prakash, T. Mathew, D. Hoole, P. M. Esteves, Q. Wang, G. Rasul, G.
A. Olah, J. Am. Chem. Soc.,
2004,
126, 15570-15776.
Aryl and heteroaryl boronic acids react with N-iodosuccinimide and
N-bromosuccinimide to give the corresponding iodo- and bromo-arenes in good
to excellent yields. The reaction is usually highly regioselective and yields
only the ipso-substituted product.
C. Thiebes, G. K. Surya Prakash, N. A. Petasis, G. A. Olah, Synlett,
1998, 141-142.
Using triethylamine as catalyst in Hunsdiecker reactions with N-halosuccinimides
as Br+ or 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 min.
J. Prakash, S. Roy, J. Org. Chem.,
2002, 67, 7861-7864.
A direct asymmetric iodination reaction of aldehydes with NIS catalyzed by a
novel axially chiral bifunctional amino alcohol represents a rare example of a
highly enantioselective synthesis of optically active α-iodoaldehydes.
T. Kano, M. Ueda, K. Maruoka, J. Am. Chem. Soc., 2008,
130, 3728-3729.
A catalytic amount of Au(PPh3)NTf2 converts readily
accessible propargylic acetates into versatile linear α-iodoenones in good to
excellent yields. Very good Z-selectivities are observed for aliphatic
propargylic acetates.
M. Yu, G. Zhang, L. Zhang, Org. Lett., 2007,
9, 2087-2090.
A sequence consisting of an electrophilic cyclization in the presence of N-iodosuccinimide
(NIS) and an 1,2-migration allows the construction of 4-iodo-3-furanones from
2-alkynyl-2-silyloxy carbonyl compounds. In a more versatile variant, AuCl3
catalyzes the tandem reaction in the presence of NIS to provide highly
substituted heterocycles in good yields.
B. Crone, S. F. Kirsch, J. Org. Chem., 2007,
72, 5435-5438.
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 phenols.
B. Karimi, A. Zamani, D. Zarayee, Tetrahedron Lett., 2004,
45, 9139-9141.
