EN300-43394895

Reagent for the selective vinylation of organic substrates

Vinylthianthrenium tetrafluoroborate is an innovative vinylating reagent. This crystalline powder with a long shelf life shows impressive results in incorporating a vinyl group as a C-2 building block. This reagent has unique properties and reactivity profile. With its broad substrate scope, vinylthianthrenium tetrafluoroborate enables effective transformations, including N-vinylation of heterocycles, vinylation of aryl boronic acids, and annulation of cyclic and heterocyclic substrates[1]. Its distinctive structure positions it as a superior performer in cross-coupling reactions. Moreover, this reagent facilitates metal-free cyclopropanation and aziridination of alkenes with XH2 (X=N, C)[2]. Recently, a bioconjugation method employing a vinyl thianthrenium salt was reported to convert cysteine residues in the proteins into a highly reactive electrophilic episulfonium intermediate. This enables one-step conjugation with various bioorthogonal nucleophiles, linking biomolecules via a stable ethylene linker. It's handy for incorporating infrared labels, post-translational modifications, or NMR probes[3].