Towards iron-catalysed suzuki biaryl cross-coupling: Unusual reactivity of 2-halobenzyl halides

Robin B. Bedford*, Timothy Gallagher, Dominic R. Pye, William Savage

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

19 Citations (Scopus)

Abstract

The reaction of 2-halobenzyl halides with the borate anion Li[(Ph)(t-Bu)Bpin] leads not only to the expected arylation at the benzyl position, but also to some Suzuki biaryl cross-coupling. Preliminary mechanistic investigations hint towards the intermediacy of benzyl iron intermediates that can either: (a) directly cross-couple with the aryl boron reagent to give observed monoarylated species, or (b) undergo oxidative addition of the aryl halide to generate the diarylated species on reaction with the boron-based nucleophile.

Original languageEnglish
Article numberss-2014-c0739-st
Pages (from-to)1761-1765
Number of pages5
JournalSynthesis (Germany)
Volume47
Issue number12
DOIs
Publication statusPublished - 16 Jun 2015

Structured keywords

  • BCS and TECS CDTs

Keywords

  • aryl
  • cross-coupling
  • iron
  • organoborate
  • Suzuki reaction

Fingerprint Dive into the research topics of 'Towards iron-catalysed suzuki biaryl cross-coupling: Unusual reactivity of 2-halobenzyl halides'. Together they form a unique fingerprint.

Cite this