Catalytic C-H/olefin coupling

Shinji Mural, Fumitoshi Kakiuchi, Shinya Sekine, Yasuo Tanaka, Asayuki Kamatani, Motohiro Sonoda, Naoto Chatani

Research output: Contribution to journalArticle

110 Citations (Scopus)

Abstract

Several ruthenium complexes have been found to catalyze the addition of the C-H bond of arenes to olefins. Phenyl methyl ketone undergoes addition at its ortho position across the double bond of trimethylvinylsilane in the presence of a catalytic amount of RuH2(CO)(PPh3)3 to give 1 : 1 and 1 : 2 coupling products. In the latter, the two ortho hydrogens have reacted. Similarly, 2-methylphenyl methyl ketone reacts with trimethylvinylsilane and triethoxyvinylsilane to give the corresponding 1 : 1 coupling products in virtually quantitative yields. The results represent a breakthrough in the chemistry of carbon-hydrogen bond cleavage by metal complexes.

Original languageEnglish
Pages (from-to)1527-1534
Number of pages8
JournalPure and Applied Chemistry
Volume66
Issue number7
DOIs
Publication statusPublished - 1994 Jan 1
Externally publishedYes

Fingerprint

Alkenes
Ketones
Olefins
Ruthenium
Coordination Complexes
Carbon Monoxide
Metal complexes
Hydrogen
Hydrogen bonds
Carbon
vinyltriethoxysilane

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Mural, S., Kakiuchi, F., Sekine, S., Tanaka, Y., Kamatani, A., Sonoda, M., & Chatani, N. (1994). Catalytic C-H/olefin coupling. Pure and Applied Chemistry, 66(7), 1527-1534. https://doi.org/10.1351/pac199466071527

Catalytic C-H/olefin coupling. / Mural, Shinji; Kakiuchi, Fumitoshi; Sekine, Shinya; Tanaka, Yasuo; Kamatani, Asayuki; Sonoda, Motohiro; Chatani, Naoto.

In: Pure and Applied Chemistry, Vol. 66, No. 7, 01.01.1994, p. 1527-1534.

Research output: Contribution to journalArticle

Mural, S, Kakiuchi, F, Sekine, S, Tanaka, Y, Kamatani, A, Sonoda, M & Chatani, N 1994, 'Catalytic C-H/olefin coupling', Pure and Applied Chemistry, vol. 66, no. 7, pp. 1527-1534. https://doi.org/10.1351/pac199466071527
Mural S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M et al. Catalytic C-H/olefin coupling. Pure and Applied Chemistry. 1994 Jan 1;66(7):1527-1534. https://doi.org/10.1351/pac199466071527
Mural, Shinji ; Kakiuchi, Fumitoshi ; Sekine, Shinya ; Tanaka, Yasuo ; Kamatani, Asayuki ; Sonoda, Motohiro ; Chatani, Naoto. / Catalytic C-H/olefin coupling. In: Pure and Applied Chemistry. 1994 ; Vol. 66, No. 7. pp. 1527-1534.
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