What question did this study set out to answer?

This work aims to synthesize sulfonyl fluorides using α-diazo masked sulfinates and to explore their reactivity.

May 9, 2026Organic Letters2 citations

α-Diazo Masked Sulfinates for the Synthesis of Sulfonyl Fluorides and Their Application in the C(sp 2 )–H Functionalization of Aryl Sulfoximines

小小森優 KHKosuke Higashida TYTatsuhiko Yoshino

Key Points

This work aims to synthesize sulfonyl fluorides using α-diazo masked sulfinates and to explore their reactivity.
Designed and developed α-diazo masked sulfinates (aDAMAS reagents) with a carbonyl group.
Utilized Ru-catalyzed reactions for the synthesis of benzothiazine-1-oxides.
Demonstrated preliminary transformation reactions of the synthesized products.
Successfully synthesized sulfonyl fluorides using aDAMAS reagents.
Demonstrated ability for C(sp2)–H functionalization in aryl sulfoximines.
Highlighted the synthetic utility of benzothiazine-1-oxides bearing sulfonyl fluoride groups.

Abstract

Masked sulfinates with sulfinate protecting groups are important precursors for sulfonyl fluorides, which are versatile synthetic intermediates and biologically useful tools. We have designed and developed α-diazo masked sulfinates with an additional carbonyl group (aDAMAS reagents). These aDAMAS reagents combine a reactive α-diazo unit and a masked sulfinate moiety to provide new opportunities for the synthesis of functionalized sulfonyl fluorides. As a demonstration of the synthetic utility of these reagents, they were utilized for the Ru-catalyzed synthesis of benzothiazine-1-oxides bearing a sulfonyl fluoride group and other preliminary transformation reactions.

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