Chemoselective Cross-Coupling Reactions with Differentiation between Two Nucleophilic Sites on a Single Aromatic Substrate

Julian Linshoeft, Annika C. J. Heinrich, Stephan A. W. Segler, Paul J. Gates, Anne Staubitz*

*Corresponding author for this work

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

39 Citations (Scopus)

Abstract

A new thiophene building block, containing both a stannyl group and a boronic ester, was prepared. From this starting material, a general, nucleophile-selective one-pot reaction was developed, exploiting the different reactivities of the Stille and Suzuki-Miyaura cross-coupling reactions. A series of aromatic electrophiles were used to demonstrate the high functional group tolerance.

Original languageEnglish
Pages (from-to)5644-5647
Number of pages4
JournalOrganic Letters
Volume14
Issue number22
DOIs
Publication statusPublished - 16 Nov 2012

Keywords

  • OLIGO(HET)ARYLENE BUILDING-BLOCKS
  • FACILE STEREOSELECTIVE-SYNTHESIS
  • HIGHLY EFFICIENT SYNTHESIS
  • THIN-FILM TRANSISTORS
  • DIFUNCTIONALIZED 1,3-DIENES
  • MOLECULAR DESIGN
  • SOLAR-CELLS
  • SUZUKI
  • THIOPHENE
  • HECK

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