Photoredox-catalyzed stereo- and regioselective vicinal fluorosulfonyl-borylation of unsaturated hydrocarbons

Abstract

The sulfur (VI) fluoride exchange (SuFEx) chemistry as the next-generation click reaction, which rely on the unique reactivity-stability balance of high valent organosulfur, has attracted extensive research interest. The synthetic...

Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides

“…Wang, Zhang and co-workers recently disclosed a photoredox-catalyzed radical fluorosulfonyl-borylation reaction of alkenes for the synthesis of vicinal fluorosulfonyl alkyl borides with IMSF as the source of FSO 2 radicals (Scheme 12). [25] It is noteworthy that this strategy provided a facile and highly efficient access to various vicinal fluorosulfonyl borides (VFSBs), which could later be used as a useful bifunctional linker for the selective assembly of different molecules.…”

Fluorosulfonyl Arylation of Alkynes via Electron Donor–Acceptor Photoactivation

“…Facilitated by organic electrochemistry, oxo-fluorosulfonylation of alkynes was achieved under air, providing a variety of β-keto sulfonyl fluorides (Scheme C, c) . In addition, Wang and co-workers disclosed a radical fluorosulfonyl borylation of alkynes to access vicinal fluorosulfonyl borides (Scheme C, d) . These established methods relied on the trapping of vinyl radicals with chlorides, hydrogen donors, oxygen, or diboron species, while the addition of the corresponding vinyl radicals to arenes has not been reported (Scheme C, e).…”

Radical Ring-Opening Fluorosulfonylation of Methylenecyclobutanols via Electron Donor–Acceptor Photoactivation

“…Recently, radical fluorosulfonylation of alkenes has emerged as an important synthetic approach to diverse sulfonyl fluoride compounds . With these methods, alkenyl sulfonyl fluorides, β-alkynyl sulfonyl fluorides, β-alkoxy sulfonyl fluorides, β-amino sulfonyl fluorides, β-hydroxy sulfonyl fluorides, β-boryl sulfonyl fluorides, and other aliphatic sulfonyl fluorides have been successfully constructed from readily available alkenes. To date, the synthesis of FSO 2 -functionalized γ,δ-unsaturated carbonyls is unknown.…”