Categories: N-S Bond Formation >
Synthesis of sulfonamides
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Recent Literature
An easy and handy synthesis of sulfonamides directly from sulfonic acids or its
sodium salts is performed under microwave irradiation, has shown a good
functional group tolerance, and is high yielding.
L. De Luca, G. Giacomelli, J. Org. Chem., 2008,
73, 3967-3969.
The combination of H2O2 and SOCl2 is a highly
reactive reagent for the direct oxidative conversion of thiol derivatives to the
corresponding sulfonyl chlorides through oxidative chlorination. Upon reaction
with amines, the corresponding sulfonamides were obtained in excellent yields in
very short reaction times.
K. Bahrami, M. M. Khodaei, M. Soheilizad, J. Org. Chem., 2009,
74, 9287-9291.
A mild and efficient reaction of amine derived sulfonate salts in the presence
of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as
solvent at room temperature gives the corresponding sulfonamides in good to
excellent yields.
M. N. S. Rad, A. Khalafi-Nezhad, Z. Asrari, S. Behrouz, Z. Amini, M. Behrouz, Synthesis, 2009,
3983-3988.
A facile and efficient indium-catalyzed sulfonylation of amines allows the
synthesis of a wide range of sulfonamides in excellent yields. The method showed
a generality for substrates including less nucleophilic and sterically hindered
anilines, and it is also applicable for preparing sulfonic esters from sulfonyl
chlorides and alcohols.
J. Yan, J. Li, D. Cheng, Synlett, 2007,
2442-2444.
In ionic liquids [Bmim][PF6] or [Bmim][BF4], a highly regioselective
N-substitution of pyrrole with alkyl halides, sulfonyl chlorides, and benzoyl
chloride gave substituted pyrroles in excellent yields. Michael addition of
pyrrole with electrophilic olefins was completed in a highly regioselective
manner to afford N-alkylpyrroles.
Z.-G. Lea, Z.-C. Chen, Y. Hu, Q.-G. Zheng, Synthesis,
2004,
1951-1954.
