Iridium-catalyzed intermolecular dehydrogenative silylation of polycyclic aromatic compounds without directing groups

Masahito Murai, Keishi Takami, Kazuhiko Takai

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

This study describes the iridium-catalyzed intermolecular dehydrogenative silylation of C(sp2)-H bonds of polycyclic aromatic compounds without directing groups. The reaction produced various arylsilanes through both Si-H and C-H bond activation, with hydrogen as the sole byproduct. Reactivity was affected by the electronic nature of the aromatic compounds, and silylation of elec-tron-deficient and polycyclic aromatic compounds proceeded efficiently. Site-selectivity was controlled predominantly by steric factors. Therefore, the current functionalization proceeded with opposite chemo- and site-selectivity compared to that observed for general electrophilic functionalization of aromatic compounds.

Original languageEnglish
Pages (from-to)4566-4570
Number of pages5
JournalChemistry - A European Journal
Volume21
Issue number12
DOIs
Publication statusPublished - Mar 16 2015

Keywords

  • C-h bond activation
  • Dehydrogenation
  • Iridium
  • Polycyclic aromatic compounds
  • Silylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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