LAUSR.org creates dashboard-style pages of related content for over 1.5 million academic articles. Sign Up to like articles & get recommendations!

Accelerating sulfonyl fluoride synthesis through electrochemical oxidative coupling of thiols and potassium fluoride in flow

Photo from wikipedia

Sulfonyl fluorides are valuable synthetic motifs which are currently of high interest due to the popularity of the sulfur (VI) fluoride exchange (SuFEx) click chemistry concept. Herein, we describe a… Click to show full abstract

Sulfonyl fluorides are valuable synthetic motifs which are currently of high interest due to the popularity of the sulfur (VI) fluoride exchange (SuFEx) click chemistry concept. Herein, we describe a flow chemistry approach to enable their synthesis through an electrochemical oxidative coupling of thiols and potassium fluoride. The reaction can be carried out at room temperature and atmospheric pressure and the yield of the targeted sulfonyl fluoride, by virtue of the short inter-electrode distance between a graphite anode and a stainless-steel cathode, reached up to 92% in only 5 min residence time compared to 6 to 36 h in batch. A diverse set of thiols (7 examples) was subsequently converted in flow. Finally, a fully telescoped process was developed which combines the electrochemical sulfonyl fluoride synthesis with a follow-up SuFEx reaction.

Keywords: chemistry; synthesis electrochemical; electrochemical oxidative; sulfonyl fluoride; oxidative coupling

Journal Title: Journal of Flow Chemistry
Year Published: 2020

Link to full text (if available)


Share on Social Media:                               Sign Up to like & get
recommendations!

Related content

More Information              News              Social Media              Video              Recommended



                Click one of the above tabs to view related content.