C-SuFEx linkage of sulfonimidoyl fluorides and organotrifluoroborates

Suqin Zhao, Daming Zeng, Ming Wang () and Xuefeng Jiang ()
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Suqin Zhao: East China Normal University
Daming Zeng: East China Normal University
Ming Wang: East China Normal University
Xuefeng Jiang: East China Normal University

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract Sulfur(VI) fluoride exchange, a new type of linkage reaction, has excellent potential for application in functional molecule linkage to prepare pharmaceuticals, biomolecules, and polymers. Herein, a C-SuFEx reaction is established to achieve fast (in minutes) linkage between sulfonimidoyl fluorides and aryl/alkyl organotrifluoroborates. Potassium organotrifluoroborates are instantaneously activated via a substoichiometric amount of trimethylsilyl triflate to afford organodifluoroboranes, releasing BF3 as an activating reagent in situ. This sulfur(VI) fluoride exchange technique is capable of forming S(VI)-C(alkyl), S(VI)-C(alkenyl) and S(VI)-C(aryl) bonds, demonstrating its broad scope. Natural products and pharmaceuticals with sensitive functional groups, such as valdecoxib, celecoxib and diacetonefructose, are compatible with this protocol, allowing the formation of diverse sulfoximines.

Date: 2024
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DOI: 10.1038/s41467-024-44998-6

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