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Radical 1-Fluorosulfonyl-2-alkynylation of Unactivated Alkenes.

ABSTRACT: Sulfonyl fluorides have found widespread use in chemical biology and drug discovery. The development of synthetic methods for the introduction of the sulfonyl fluoride moiety is therefore of importance. Herein, a transition-metal-free radical 1,2-difunctionalization of unactivated alkenes via FSO₂ -radical addition with subsequent vicinal alkynylation to access β-alkynyl-fluorosulfonylalkanes is presented. Alkynyl sulfonyl fluorides are introduced as highly valuable bifunctional radical trapping reagents that also serve as FSO₂ -radical precursors. The β-alkynyl-fluorosulfonylalkanes obtained in these transformations can be readily diversified by using SuFEx click chemistry to obtain sulfonates and sulfonamides.

SUBMITTER: Frye NL

PROVIDER: S-EPMC9305502 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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Radical 1-Fluorosulfonyl-2-alkynylation of Unactivated Alkenes.

Frye Nils Lennart NL Daniliuc Constantin G CG Studer Armido A

Angewandte Chemie (International ed. in English) 20220127 12

Sulfonyl fluorides have found widespread use in chemical biology and drug discovery. The development of synthetic methods for the introduction of the sulfonyl fluoride moiety is therefore of importance. Herein, a transition-metal-free radical 1,2-difunctionalization of unactivated alkenes via FSO<sub>2</sub> -radical addition with subsequent vicinal alkynylation to access β-alkynyl-fluorosulfonylalkanes is presented. Alkynyl sulfonyl fluorides are introduced as highly valuable bifunctional radic ...[more]

PMID: 34958162

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