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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.