Iridium-catalyzed dehydrogenative silylation of azulenes based on regioselective C-H bond activation

Masahito Murai, Keishi Takami, Hirotaka Takeshima, Kazuhiko Takai

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Use of an iridium catalyst allowed the efficient dehydrogenative functionalization of C-H bonds of azulenes with the production of hydrogen as the sole byproduct. The reaction occurred with excellent chemo- and regioselectivities to provide 2-silylazulenes even without any directing groups. Effective conjugation through the 2-position of the azulene ring was demonstrated by the unique stimuli-responsiveness against an acid-base reaction.

Original languageEnglish
Pages (from-to)1798-1801
Number of pages4
JournalOrganic Letters
Volume17
Issue number7
DOIs
Publication statusPublished - Apr 3 2015

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Azulenes
Iridium
Regioselectivity
iridium
Byproducts
Hydrogen
Chemical activation
activation
azulene
Catalysts
Acids
conjugation
stimuli
catalysts
acids
rings
hydrogen

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Iridium-catalyzed dehydrogenative silylation of azulenes based on regioselective C-H bond activation. / Murai, Masahito; Takami, Keishi; Takeshima, Hirotaka; Takai, Kazuhiko.

In: Organic Letters, Vol. 17, No. 7, 03.04.2015, p. 1798-1801.

Research output: Contribution to journalArticle

Murai, Masahito ; Takami, Keishi ; Takeshima, Hirotaka ; Takai, Kazuhiko. / Iridium-catalyzed dehydrogenative silylation of azulenes based on regioselective C-H bond activation. In: Organic Letters. 2015 ; Vol. 17, No. 7. pp. 1798-1801.
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