N-Chlorosuccinimide (NCS)
N-Chlorosuccinimide (NCS) is a chlorinating and oxidizing agent that is used as source for chlorine in radical reactions and various electrophilic additions.
Recent Literature
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.
A mild palladium-catalyzed, regioselective chlorination, bromination, and
iodination of arene C-H bonds using N-halosuccinimides as oxidants is
described. These transformations can provide products that are complementary
to those obtained via conventional electrophilic aromatic substitution
reactions.
D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford, Org. Lett.,
2006,
8, 2523-2526.
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 smooth oxidation of several thiol derivatives by a combination of N-chlorosuccinimide
and dilute hydrochloric acid afforded the corresponding sulfonyl chlorides in
good yield.
A. Nishiguchi, K. Maeda, S. Miki,
Synthesis, 2006, 4131-4134.
