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

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

doi:10.1021/ja074350y

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

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

化学科

研究成果: Article › 査読

108 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	12902-12903
ページ数	2
ジャーナル	Journal of the American Chemical Society
巻	129
号	43
DOI	https://doi.org/10.1021/ja074350y
出版ステータス	Published - 2007 10月 31

ASJC Scopus subject areas

触媒
化学 (全般)
生化学
コロイド化学および表面化学

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10.1021/ja074350y

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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.",

author = "Yudai Sugawara and Wataru Yamada and Shunsuke Yoshida and Taketo Ikeno and Tohru Yamada",

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AU - Yamada, Wataru

AU - Yoshida, Shunsuke

AU - Ikeno, Taketo

AU - Yamada, Tohru

PY - 2007/10/31

Y1 - 2007/10/31

N2 - 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.

AB - 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.

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

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