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, efficient, Cu(I)-catalyzed method for the synthesis of aryl chlorides
from arylboronic acids is particularly useful for the conversion of
electron-deficient arylboronic acids to aryl chlorides, a transformation that is
inefficient in the absence of Cu catalysis.
H. Wu, J. Hynes, Jr., Org. Lett., 2010,
12, 1192-1195.
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 fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst shows
good activity and enantioselectivity for direct α-chlorination of aldehydes
using N-chlorosuccinimide (NCS) as the chlorine source. The catalyst can
be recovered from the reaction mixture by fluorous solid-phase extraction with
excellent purity for direct reuse.
L. Wang, C. Cai, D. P. Curran, W. Zhang, Synlett, 2010, 433-436.
A direct organocatalytic enantioselective α-chlorination of aldehydes
proceeds for a series of different aldehydes with NCS as the chlorine source
using easily available catalysts such as L-proline amide and (2R,5R)-diphenylpyrrolidine.
The α-chloro aldehydes are obtained in very good yield and high
enantioselectivity.
N. Halland, A. Braunton, S. Bachmann, M. Marigo, K. A. Jorgensen, J. Am. Chem. Soc.,
2004,
126, 4790-4791.
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.
