Novel green chemistry: A safe, low-cost, and eco-friendly conversion process for the synthesis of sulfonyl fluorides, a world first!
A research group including researchers from Osaka University has developed a method to safely and cost-effectively convert thiols and disulfides, which are easily accessible raw materials, into sulfonyl fluorides.
Osaka, Japan – For the first time in the world, thiols and disulfides were converted into sulfonyl fluorides using SHC5® and KF, expanding "click chemistry" with high efficiency and low environmental impact. This green process, yielding only NaCl and KCl as byproducts, is expected to become the preferred method in chemical and industrial synthesis.
The concept of "click chemistry” is known for its high chemical selectivity, high yield, and rapid connection of molecules. Since its inception, click chemistry has demonstrated broad utility across various fields, including synthesis, materials science, chemical biology, and pharmaceutical development, garnering immense popularity.
However, sulfonyl fluoride is a key compound in the sulfur-fluorine exchange (SuFEx) click reaction, which links molecules together, and its synthesis initially required the use of SO2F2 gas or KHF2, both of which are highly toxic and difficult to handle. To achieve the safe and environmentally-friendly synthesis of sulfonyl fluoride, synthetic chemists have explored various chemical reaction processes.
In this study, it was developed for the first time in the world that sulfonyl fluoride can be efficiently synthesized by reacting the easily-handled and highly-reactive SHC5® and KF (potassium fluoride) with thiols or disulfides. This is a green synthetic process that produces only non-toxic sodium and potassium salts as by-products, resulting in minimal environmental impact.
This chemical reaction enabled the environmentally-friendly and tailor-made synthesis of a broad scope of sulfonyl fluorides containing aromatic, aliphatic, and heterocyclic groups.
The synthetic protocol is very simple, enabling the low-cost, scalable, and safe production of sulfonyl fluorides. This new method is expected to become the first choice for sulfonyl fluoride synthesis in both the chemical and industrial sectors.
"Developing new organic synthetic protocols to create useful compounds, such as pharmaceuticals, is a highly important research theme, particularly from the perspective of the Sustainable Development Goals (SDGs)," says corresponding authors of the study Masayuki Kirihara, Shinobu Takizawa, and Mohamed S. H. Salem. "Furthermore, developing reaction processes that consider the environmental impact of by-products is becoming increasingly important. We will continue to disseminate research from Japan that focuses on the green synthesis of useful compounds with ripple effects across various fields."
The article, “Green and Efficient Protocols for the Synthesis of Sulfonyl Fluorides Using Potassium Fluoride as the Sole Fluorine Source,” was published in ACS Sustainable Chemistry & Engineering at DOI: https://doi.org/10.1021/acssuschemeng.4c03951
Summary
A research group including researchers from SANKEN (The Institute of Scientific and Industrial Research) at Osaka University has developed a safe, cost-effective, and environmentally-friendly method to synthesize sulfonyl fluorides. By reacting thiols and disulfides with SHC5® and potassium fluoride, they achieved a green synthesis process with non-toxic by-products. This method simplifies the production of sulfonyl fluorides, making it suitable for chemical and industrial applications, aligning with Sustainable Development Goals.
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Novel green #chemistry: safe, low-cost, and #eco-friendly conversion process for the #synthesis of #sulfonyl #fluorides, world first! @osaka_univ_e
Primary Keyword
Physical sciences
Additional Keywords
Organic synthesis
Organic reactions
