Categories: S=O Bond Formation >
Synthesis of sulfonyl chlorides
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.