Issue 7, 2014
From the journal:

Chemical Science

Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones†

Megumi Okada,a   Takahide Fukuyama,a   Keiichi Yamada,a   Ilhyong Ryu,*a   Davide Ravellib  and  Maurizio Fagnoni*b  

* Corresponding authors

a Department of Chemistry, Graduate School of Science Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
E-mail: ryu@c.s.osakafu-u.ac.jp
Fax: +81 72 254 9695
Tel: +81 72 254 9695

b PhotoGreen Lab, Department of Chemistry, University of Pavia, viale Taramelli 12, 27100 Pavia, Italy
E-mail: fagnoni@unipv.it
Fax: +39 0382 987323
Tel: +39 0382 987198

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.

Graphical abstract: Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones

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Article information

DOI
https://doi.org/10.1039/C4SC01072H
Article type
Edge Article
Submitted
11 Apr 2014
Accepted
08 May 2014
First published
08 May 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 2893-2898

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Sunlight photocatalyzed regioselective β-alkylation and acylation of cyclopentanones

M. Okada, T. Fukuyama, K. Yamada, I. Ryu, D. Ravelli and M. Fagnoni, Chem. Sci., 2014, 5, 2893 DOI: 10.1039/C4SC01072H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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