Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones

Megumi Okada; Takahide Fukuyama; Keiichi Yamada; Ilhyong Ryu; Davide Ravelli; Maurizio Fagnoni

doi:10.1039/c4sc01072h

Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones

Megumi Okada, Takahide Fukuyama, Keiichi Yamada, Ilhyong Ryu^*, Davide Ravelli, Maurizio Fagnoni

^*Corresponding author for this work

Department of Applied Chemistry

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

83 Scopus citations

Abstract

Sunlight-induced direct regioselective β-alkylation of cyclopentanones with electron-deficient alkenes was accomplished by using tetrabutylammonium decatungstate (TBADT) as the catalyst. The regiochemistry can be rationalized by a polar transition state for an S_H2 reaction. In the presence of CO, the reaction gave the three-component β-acylation product in good yield.

Original language	English
Pages (from-to)	2893-2898
Number of pages	6
Journal	Chemical Science
Volume	5
Issue number	7
DOIs	https://doi.org/10.1039/c4sc01072h
State	Published - 1 Jan 2014

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title = "Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones",

abstract = "Sunlight-induced direct regioselective β-alkylation of cyclopentanones with electron-deficient alkenes was accomplished by using tetrabutylammonium decatungstate (TBADT) as the catalyst. The regiochemistry can be rationalized by a polar transition state for an SH2 reaction. In the presence of CO, the reaction gave the three-component β-acylation product in good yield.",

author = "Megumi Okada and Takahide Fukuyama and Keiichi Yamada and Ilhyong Ryu and Davide Ravelli and Maurizio Fagnoni",

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T1 - Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones

AU - Okada, Megumi

AU - Fukuyama, Takahide

AU - Yamada, Keiichi

AU - Ryu, Ilhyong

AU - Ravelli, Davide

AU - Fagnoni, Maurizio

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Sunlight-induced direct regioselective β-alkylation of cyclopentanones with electron-deficient alkenes was accomplished by using tetrabutylammonium decatungstate (TBADT) as the catalyst. The regiochemistry can be rationalized by a polar transition state for an SH2 reaction. In the presence of CO, the reaction gave the three-component β-acylation product in good yield.

AB - Sunlight-induced direct regioselective β-alkylation of cyclopentanones with electron-deficient alkenes was accomplished by using tetrabutylammonium decatungstate (TBADT) as the catalyst. The regiochemistry can be rationalized by a polar transition state for an SH2 reaction. In the presence of CO, the reaction gave the three-component β-acylation product in good yield.

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U2 - 10.1039/c4sc01072h

DO - 10.1039/c4sc01072h

M3 - Article

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JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

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ER -

Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones

Abstract

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