The sulfur(VI) fluoride exchange (SuFEx) chemistry that rely on the unique reactivity–stability balance of high valent organosulfur has emerged as a promising topic for the next-generation click reaction. Sulfonyl fluorides as the most widely used connective hubs of SuFEx click reaction have attracted enormous attention and find widespread applications in the fields of chemical biology, drug discovery and material science. Sulfonyl fluoride (SO2F2) is a greenhouse gas with highly symmetrical orbital and considerable S-F bond dissociation energy. Therefore, the activation of sulfonyl fluoride represents great challenge and in high demand. Although SO2F+ anion could be achieved from sulfonyl fluoride, the electron transfer (SET) process of SO2F2 for radical fluorosulfonylation has not been disclosed. We have designed and prepared a series of bench-stable fluorosulfonylating reagents from SO2F2 gas and N-heteroarenes, which could generate SO2F. for various radical additions. These reagents demonstrate superior reactivity and broad substrate scope, which provide versatile sites for SuFEx click reactions.

Single electron activation of sulfonyl fluoride

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