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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

106 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 language	English
Pages (from-to)	12902-12903
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	43
DOIs	https://doi.org/10.1021/ja074350y
Publication status	Published - 2007 Oct 31

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja074350y

Cite this

@article{1165b1a8069a4533ac835023063a2a68,

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

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",

year = "2007",

month = oct,

day = "31",

doi = "10.1021/ja074350y",

language = "English",

volume = "129",

pages = "12902--12903",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "43",

}

TY - JOUR

T1 - Carbon dioxide-mediated catalytic rearrangement of propargyl alcohols into α,β-unsaturated ketones

AU - Sugawara, Yudai

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.

UR - http://www.scopus.com/inward/record.url?scp=35948942005&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35948942005&partnerID=8YFLogxK

U2 - 10.1021/ja074350y

DO - 10.1021/ja074350y

M3 - Article

C2 - 17918841

AN - SCOPUS:35948942005

SN - 0002-7863

VL - 129

SP - 12902

EP - 12903

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 43

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this