Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides.

ABSTRACT: We disclose a method for the dibenzylation of alkenylarenes with benzyl bromides using iron powder. This reaction generates branched alkyl scaffolds adorned with functionalized aryl rings through the formation of two new C(sp³)-C(sp³) bonds at the vicinal carbons of alkenes. This protocol tolerates electron-rich, electron-neutral, and electron-poor benzyl bromides and alkenylarenes. Mechanistic studies suggest the formation of benzylic radical intermediates as a result of single-electron transfer from the iron, which is intercepted by alkenylarenes.

SUBMITTER: Lux DM 

PROVIDER: S-EPMC11450104 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature