Construction of Biaryl Scaffolds from Iodoarenes and C−H Heteroarenes Using an Amide Base Generated in situ from Aminosilane and Fluoride Anion

Masanori Shigeno, Yusuke Kai, Tetsuya Yamada, Kazutoshi Hayashi, Kanako Nozawa-Kumada, Charline Denneval, Yoshinori Kondo

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Iodoarenes and C−H heteroarenes are coupled to form a biaryl in the presence of an amide base generated in situ from tetramethylammonium fluoride (TMAF) and hexamethyldisilazane (HMDS) by homolytic aromatic substitution (HAS). This reaction can be used with electron-rich, -deficient, and ortho-substituted haloarenes. Both electron-rich and -deficient C−H heteroarenes can also be utilized. Involvement of a radical intermediate was confirmed by radical inhibition experiments, deuterium-labelling experiments, and EPR spectral measurements. Enhancement of the reactivity of electron-rich N-methylpyrrole was observed in the presence of electron-poor phenazine or pyrazine.

Original languageEnglish
Pages (from-to)2082-2086
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume7
Issue number10
DOIs
Publication statusPublished - 2018 Oct

Keywords

  • Amide base
  • Anions
  • Biaryl
  • Homolytic aromatic substitution
  • Radicals

ASJC Scopus subject areas

  • Organic Chemistry

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