Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones

Yudai Sugawara, Wataru Yamada, Shunsuke Yoshida, Taketo Ikeno, Tohru Yamada

Research output: Contribution to journalArticle

85 Citations (Scopus)

Abstract

In the presence of a catalytic amount of a silver salt with DBU under a CO2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into the corresponding α,β-unsaturated carbonyl compounds in high yield. An isotopic experiment using C18O2 revealed that carbon dioxide mediated the rearrangement via an intramolecular nucleophilic attack on the alkyne activated by the silver catalyst.

Original languageEnglish
Pages (from-to)12902-12903
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number43
DOIs
Publication statusPublished - 2007 Oct 31

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Ketones
Silver
Carbon Dioxide
Carbon dioxide
Alcohols
Carbonyl compounds
Alkynes
Atmosphere
Salts
Catalysts
Experiments
propargyl alcohol

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones. / Sugawara, Yudai; Yamada, Wataru; Yoshida, Shunsuke; Ikeno, Taketo; Yamada, Tohru.

In: Journal of the American Chemical Society, Vol. 129, No. 43, 31.10.2007, p. 12902-12903.

Research output: Contribution to journalArticle

Sugawara, Yudai ; Yamada, Wataru ; Yoshida, Shunsuke ; Ikeno, Taketo ; Yamada, Tohru. / Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones. In: Journal of the American Chemical Society. 2007 ; Vol. 129, No. 43. pp. 12902-12903.
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