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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 |

REPOSITORIES: biostudies-literature

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