Polarity Transduction Enables the Formal Electronically Mismatched Radical Addition to Alkenes.

ABSTRACT: The formation of carbon-carbon bonds via the intermolecular addition of alkyl radicals to alkenes is a cornerstone of organic chemistry and plays a central role in synthesis. However, unless specific electrophilic radicals are involved, polarity matching requirements restrict the alkene component to be electron deficient. This limits the scope of a fundamentally important carbon-carbon bond forming process that could otherwise be more universally applied. Herein, we introduce a polarity transduction strategy that formally overcomes this electronic limitation. Vinyl sulfonium ions are demonstrated to react with carbon-centered radicals, giving adducts that undergo in situ or sequential nucleophilic displacement to provide products that would be inaccessible via traditional met

SUBMITTER: Paul S 

PROVIDER: S-EPMC9912259 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature