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. 2024 Nov 15;89(22):16292-16299.
doi: 10.1021/acs.joc.3c02548. Epub 2024 Apr 4.

Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides

Daniel M Lux  1 , Daniel J Lee  1 , Rishi R Sapkota  1 , Ramesh Giri  1
Affiliations

Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides

Daniel M Lux et al. J Org Chem. .

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.

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Conflict of interest statement

The authors declare no competing financial interests.

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