A Zinc Catalyzed C(sp3)−C(sp2) Suzuki–Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates

Richard J. Procter, Jay J. Dunsford, Philip J. Rushworth, David G. Hulcoop, Richard A. Layfield, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The Suzuki–Miyaura (SM) reaction is one of the most important methods for C−C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr2, in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.

Original languageEnglish
Pages (from-to)15889-15893
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number63
Early online date27 Sep 2017
DOIs
Publication statusE-pub ahead of print - 27 Sep 2017

Keywords

  • alkylation
  • boron
  • cross-coupling
  • transmetallation
  • zincate

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