A novel and efficient method enables the preparation of sulfonyl chlorides from sulfonic acids using TAPC as chlorinating agent. Mild reaction conditions, short reaction times, high efficiency, cost-effectiveness, and facile isolation of the desired products make the present methodology a practical alternative and will provide a valuable synthetic tool for various pharmaceutical applications.
K. Bahrami, Synlett, 2011, 2671-2674.
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.