Nucleophile-Selective Cross-Coupling Reactions with Vinyl and Alkynyl Bromides on a Dinucleophilic Aromatic Substrate

Lu Ying He, Mathias Schulz-Senft, Birk Thiedemann, Julian Linshoeft, Paul J. Gates, Anne Staubitz*

*Corresponding author for this work

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

8 Citations (Scopus)

Abstract

A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.

Original languageEnglish
Pages (from-to)2498-2502
Number of pages5
JournalEuropean Journal of Organic Chemistry
Early online date27 Feb 2015
DOIs
Publication statusPublished - 2015

Keywords

  • C-C coupling
  • Chemoselectivity
  • Cross-coupling
  • Palladium
  • Sulfur heterocycles

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