Synthesis of functionalized o-, m-, and p-terphenyl derivatives by consecutive cross-coupling reactions of triazene-substituted arylboronic esters

Ching Yuan Liu, Andrey Gavryushin, Paul Knochel

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54 Scopus citations

Abstract

Triazene-substituted arylboronic esters were prepared readily from the corresponding aryl magnesium derivatives and shown to function as a new class of donor-acceptor-substituted coupling reagents. The selective functionalization of these aromatic derivatives led to a wide variety of terphenyl derivatives in which the original bifunctional unit (often further substituted with another functional group) formed the central aromatic ring. The functionalized terphenyl derivatives were formed in two efficient cross-coupling steps from the triazene-substituted boronic esters: Suzuki cross-coupling with an aryl halide was followed by BF3·OEt2-induced palladium-catalyzed coupling of the diazonium salt generated in situ from the triazene with an arylboronic acid.

Original languageEnglish
Pages (from-to)1020-1030
Number of pages11
JournalChemistry - An Asian Journal
Volume2
Issue number8
DOIs
StatePublished - 2007

Keywords

  • Boronic esters
  • Cross-coupling
  • Synthetic methods
  • Terphenyls
  • Triazenes

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