A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes

Alexander S. Dudnik, Natalia Chernyak, Chunhui Huang, Vladimir Gevorgyan

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Abstract

A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.

Original languageEnglish (US)
Pages (from-to)8729-8732
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number46
DOIs
Publication statusPublished - Nov 8 2010
Externally publishedYes

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Keywords

  • benzynes
  • C-H activation
  • halogenation
  • palladium
  • siloles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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