Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides

Daniel M. Lux, Daniel J. Lee, Rishi R. Sapkota, Ramesh Giri

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
JournalJournal of Organic Chemistry
DOIs
StateAccepted/In press - 2023

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides'. Together they form a unique fingerprint.

Cite this