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Synthesis of sulfonyl chlorides
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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.
Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very
efficient reagent for the direct oxidative conversion of thiols and disulfides
into the corresponding sulfonyl chlorides with high purity through oxidative
chlorination. Excellent yields, very short reaction times, mild reaction
conditions, and the avoidance of harsh reagents are the main advantages of this
method.
K. Bahrami, M. M. Khodaei, M. Soheilizad, Synlett, 2009,
2773-2776.
A mixture of nitrate salt and chlorotrimethylsilane is a mild and efficient
reagent for the direct oxidative chlorination of thiols and disulfides to the
corresponding sulfonyl chlorides in excellent yields. Sulfides and sulfoxides
were also found to undergo oxidation to sulfones. In most cases these reactions
are highly selective, simple, and clean, affording products in high yield and
purity.
G. K. S. Prakash, T. Mathew, C. Panja, G. A. Olah, J. Org. Chem., 2007,
72, 5847-5850.
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.
In situ preparation of sulfonyl chlorides from thiols by oxidation with N-chlorosuccinimide
(NCS), tetrabutylammonium chloride, and water followed by reaction with amine or
sodium azide in the same reaction vessel enables a convenient synthesis of
sulfonamides and sulfonyl azides.
H. Veisi, R. Ghorbani-Vaghei, S. Hemmati, J. Mahmoodi, Synlett, 2011,
2315-2320.