Ru3(CO)12-catalyzed silylation of benzylic C-H bonds in arylpyridines and arylpyrazoles with hydrosilanes via C-H bond cleavage

Fumitoshi Kakiuchi, Kazuyuki Tsuchiya, Mitsutaka Matsumoto, Eiichiro Mizushima, Naoto Chatani

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Abstract

Ruthenium-catalyzed silylation of sp3 C-H bonds at a benzylic position with hydrosilanes gave benzylsilanes. For this silylation reaction, Ru3(CO)12 complex showed high catalytic activity. This silylation proceeded at the methyl C-H bond selectively. For this silylation reaction, pyridyl and pyrazolyl groups, and the imino group in hydrazones, can function as a directing group. Several hydrosilanes involving triethyl-, dimethylphenyl-, tert-butyldimethyl-, and triphenylsilanes can be used as a silylating reagent. Coordination of an sp2 nitrogen atom to the ruthenium complex is important for achieving this silylation reaction.

Original languageEnglish
Pages (from-to)12792-12793
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number40
Publication statusPublished - 2004 Oct 13
Externally publishedYes

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Ruthenium
Carbon Monoxide
Hydrazones
Catalyst activity
Nitrogen
Atoms

ASJC Scopus subject areas

  • Chemistry(all)

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Ru3(CO)12-catalyzed silylation of benzylic C-H bonds in arylpyridines and arylpyrazoles with hydrosilanes via C-H bond cleavage. / Kakiuchi, Fumitoshi; Tsuchiya, Kazuyuki; Matsumoto, Mitsutaka; Mizushima, Eiichiro; Chatani, Naoto.

In: Journal of the American Chemical Society, Vol. 126, No. 40, 13.10.2004, p. 12792-12793.

Research output: Contribution to journalArticle

Kakiuchi, Fumitoshi ; Tsuchiya, Kazuyuki ; Matsumoto, Mitsutaka ; Mizushima, Eiichiro ; Chatani, Naoto. / Ru3(CO)12-catalyzed silylation of benzylic C-H bonds in arylpyridines and arylpyrazoles with hydrosilanes via C-H bond cleavage. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 40. pp. 12792-12793.
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AU - Chatani, Naoto

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