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

Masahito Murai; Keishi Takami; Hirotaka Takeshima; Kazuhiko Takai

doi:10.1021/acs.orglett.5b00575

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 journal › Article › peer-review

64 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 language	English
Pages (from-to)	1798-1801
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.5b00575
Publication status	Published - Apr 3 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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T1 - Iridium-catalyzed dehydrogenative silylation of azulenes based on regioselective C-H bond activation

AU - Murai, Masahito

AU - Takami, Keishi

AU - Takeshima, Hirotaka

AU - Takai, Kazuhiko

PY - 2015/4/3

Y1 - 2015/4/3

N2 - 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.

AB - 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.

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

Abstract

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