Straightforward and Sustainable Synthesis of Sulfonamides in Water under Mild Conditions

Abstract

Ideally, a sustainable chemical synthesis should involve the use of non‐toxic solvents and reactants, easy separations and purification by energy‐efficient processes. In this context, reconsidering the synthesis of widely used drugs is especially timely and should allow important benefits to be obtained in terms of environmental impact. Sulfonamides are pertinent as their synthesis generally requires the use of toxic and/or hard‐to‐remove solvents such as dichloromethane, DMF and DMSO. In addition, toxic and highly reactive sulfur‐containing sources such as sulfonyl chloride are often involved and coupled with amines. Moreover, the latter may exhibit some toxicity and are generally difficult to purify. Herein, we disclose the unprecedented and sustainable synthesis of sulfonamides by using sodium sulfinate as a commercial and stable sulfur source and nitroarenes as the nitrogen‐containing reactant. In addition, under the optimized conditions only water is used as a “green” solvent and the products are collected by simple filtration.

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…Afterwards, the Andrioletti group described the reductive-sulfonylation of nitroarenes and sulfinate salts in the presence of sodium bisulfite (NaHSO 3 ) alone as the reducing agent in water at 60 °C ( Scheme 36A ). 80 A variety of water-soluble nitroarenes were successfully converted into the corresponding sulfonamides in 25–78% yields. This protocol was restricted to only electron-withdrawing nitroarenes.…”

Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry

“…Dimethylformamide) or surprisingly reactive poisonous beginning substances (e.g. thionyl chloride) [198].Recently, promising methods for synthesizing sulfonamide compounds in a"green" or non-toxic way have been published that demonstrated the synthesis without any organic solvents or reactive sulfur-sources like sulfonyl chloride [198,199]. To summarize, a sulfonamide-based compounds have one of the broadest ranges of biological activities among drug molecules.This assets of sulfa-drugs combined with their structural versatility and big amount of data available cause them to splendid applicants for developing extra effective and more secure alternatives to the modern drugs for numerous diseases, complex or higher understood alike.…”

Chain-End Functionality: The Key Factor toward Fluoropolymer Thermal Stability

“…39 Because of their stability toward air and moisture, they are mainly used as alternatives to sulfonyl chlorides in the preparation of sulfonamides. 40 Furthermore, sulfinates can also be used to afford organic radicals under oxidative conditions. 41 One significant example for the utility and the versatility of this synthetic approach is the radical trifluoromethylation of organic compounds using sodium trifluoromethanesulfinate (called the Langlois reagent).…”

“…They are synthesized from the corresponding sulfonyl halides − or by the addition of an organometallic reagent to sulfur dioxide . Because of their stability toward air and moisture, they are mainly used as alternatives to sulfonyl chlorides in the preparation of sulfonamides . Furthermore, sulfinates can also be used to afford organic radicals under oxidative conditions .…”