N-Bromosuccinimide (NBS)
N-Bromosuccinimide (NBS) is a brominating and oxidizing agent that is used as source for bromine in radical reactions (for example: allylic brominations) and various electrophilic additions. The NBS bromination of substrates such as alcohols and amines, followed by elimination of HBr in the presence of a base, leads to the products of net oxidation in which no bromine has been incorporated.
Name Reactions
Recent Literature
An efficient and user-friendly procedure has been
developed for the oxidative deprotection of tetrahydropyranyl (THP) ethers with
N-bromosuccinimide (NBS) using β-cyclodextrin (β-CD) in water. A series
of tetrahydropyranyl ethers were oxidatively deprotected at room temperature in
impressive yields.
M. Narender, M. S. Reddy, K. R. Rao, Synthesis, 2004,
1741-1743.
Unsaturated compounds such as alkenes, alkynes, allenes, and
methylenecyclopropanes (MCPs) can be dibrominated within minutes by NBS and
lithium bromide in THF at room temperature in good to excellent yields under
mild conditions.
L.-X. Shao, M. Shi, Synlett,
2006, 1269-1271.
L.-X. Shao, M. Shi, Synlett,
2006, 1269-1271.
L.-X. Shao, M. Shi, Synlett,
2006, 1269-1271.
A convenient and efficient method for aminobromination of
alkylidenecyclopropanes is reported. This is exemplified in the stereoselective
preparation of N-[(Z)-3-bromobut-3-en-1-yl]-p-toluenesulfonamides
by using p-toluenesulfonamide and N-bromosuccinimide (NBS) as
nitrogen and bromine sources, respectively.
X. Huang, W.-J. Fu,
Synthesis, 2006, 1016-1017.
Highly regioselective nuclear bromination of activated
aromatic and heteroaromatic compounds has been accomplished using N-bromosuccinimide
in tetrabutylammonium bromide. Predominant
para-selective monobromination of activated aromatics such as phenols and
anilines, rate acceleration of bromination for moderately activated and less
reactive substrates on addition of acidic montmorillonite K-10 clay, with or
without microwave assistance, are the notable features of this protocol.
N. C. Ganguly, P. De. S. Dutta, Synthesis, 2005, 1103-1108.
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.
J. Prakash, S. Roy, J. Org. Chem.,
2002, 67, 7861-7864.
(E)-β-Arylvinyl bromides were readily prepared
in a short reaction time (1-2 min) by microwave irradiation of the corresponding
3-arylpropenoic acids in the presence of N-bromosuccinimide and a
catalytic amount of lithium acetate.
C. Kuang, Q. Yang, H. Senboku, M. Tokuda, Synthesis, 2005,
1319-1325.
A new procedure for aminobromination of olefins gives vicinal bromoamine derivatives in high yields using Cu, Mn, or V
catalysts with
p-toluenesulfonamide as nitrogen source and N-bromosuccinimide
(NBS) as bromine source. Excellent regio- and stereoselectivity is shown for different olefinic substrates as well as transition metal
catalysts.
V. V. Thakur, S. K. Talluri, A. Sudalai, Org. Lett., 2003,
5, 861-864.
New methodology for the synthesis of variously substituted 2-oxazolines and
one dihydrooxazine using aldehydes, amino alcohols, and N-bromosuccinimide as an oxidizing agent is described. This one-pot synthesis is characterized by mild
reaction conditions, broad scope, high yields, and its preparative simplicity.
K. Schwekendiek, F. Glorius,
Synthesis, 2006, 2996-3002.
A versatile and highly efficient Zn(OTf)2-catalyzed one-pot
reaction of alkenes, NBS, nitriles, and TMSN3 gives various 1,5-disubstituted
tetrazoles containing an additional α-bromo functionality of the N1-alkyl
substituent.
S. Hajra, D. Sinha, M. Bhowmick, J. Org. Chem., 2007,
72, 1852-1855.
A one-pot synthesis of aryl sulfones from primary alcohols is described.
Alcohols were treated with N-bromosuccinimide and triphenylphosphine,
followed by addition of sodium arenesulfinate with a catalytic amount of
tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.
T. Murakami, K. Furusawa, Synthesis,
2002, 479-482.
