Categories: C-N Bond Formation >
Synthesis of sulfonamides
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Recent Literature
A new, simple method for the conversion of alcohols to tosylamides is
presented.
M. C. Marcotullio, V. Campagna, S. Sternativo, F. Costantino, M. Curini,
Synthesis, 2006, 2760-2766.
The arylation of N-H and O-H containing compounds at room temperature with
phenylboronic acids is promoted in the presence of cupric acetate and a tertiary
amine. Substrates include phenols, amines, anilines, amides, imides, ureas,
carbamates, and sulfonamides.
D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winteres, Tetrahedron Lett.,
1998, 39, 2933-2936.
An efficient, mild and transition-metal-free N-arylation of amines,
sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has
been achieved by using various o-silylaryl triflates in the presence of CsF.
Z. Liu, R. C. Larock, J. Org. Chem., 2006,
71, 3198-3209.
A range of enol triflates can be coupled with amides, carbamates, and
sulfonamides using palladium catalysis. This method allows the synthesis of
enamides, which may not be readily available by other means.
D. J. Wallace, D. J. Klauber, C.-Y. Chen, R. P.
Volante, Org. Lett., 2003, 5, 4749-4752.
A copper-catalyzed amidation of allylic and benzylic C-H is applicable to the
coupling of a diverse set of hydrocarbon species with aryl, heteroaryl, and
alkyl sulfonamides and is tolerant of a variety of functional groups.
G. Pelletier, D. A. Powell, Org. Lett., 2006,
8, 6031-6034.
An efficient amidation reaction of saturated C-H bonds catalyzed by a unique
disilver(I) complex is reported. The reaction is stereospecific and practical
for the construction of amine-containing molecules.
Y. Cui, C. He, Angew. Chem. Int. Ed., 2004, 43, 4210-4212.
A simple addition of phenols, carboxylic acids, and protected amines to
olefins can be catalyzed by triflic acid. A low concentration of triflic
acid and control of the reaction temperature help to tolerate functional
groups, such as methoxyl substitution on aromatics.
Z. Li, J. Zhang, C. Brouwer, C.-G. Yang, N. W. Reich, C. He, Org. Lett.,
2006,
8, 4175-4178.
Ph3PAuOTf catalyzes efficient intra- and intermolecular
hydroamination of unactivated olefins with sulfonamides.
J. Zhang, C.-G. Yang, C. He, J. Am. Chem. Soc.,
2006,
128, 1798-1799.
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.
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