Ruthenium-Catalyzed Monoalkenylation of Aromatic Ketones by Cleavage of Carbon-Heteroatom Bonds with Unconventional Chemoselectivity

Hikaru Kondo, Nana Akiba, Takuya Kochi, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Ruthenium-catalyzed selective monoalkenylation of ortho C-O or C-N bonds of aromatic ketones was achieved. The reaction allowed the direct comparison of the relative reactivities of the cleavage of different carbon-heteroatom bonds, thus suggesting an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved. Smaller is better: The title reaction for ortho C-O and C-N bonds of aromatic ketones was achieved. Direct comparison of the cleavage of the carbon-heteroatom bonds suggested an unconventional chemoselectivity, where smaller, more-electron-donating groups are more easily cleaved. Selective monofunctionalization of C-O bonds in the presence of ortho C-H bonds was also achieved.

Original languageEnglish
Pages (from-to)9293-9297
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number32
DOIs
Publication statusPublished - 2015 Aug 1

Keywords

  • boron
  • chemoselectivity
  • ruthenium
  • substituent effects
  • synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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