Issue 10, 2010
From the journal:

Chemical Communications

Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones†

Ryo Shintani,*a   Takaoki Tsuji,a   Soyoung Parka  and  Tamio Hayashi*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan
E-mail: shintani@kuchem.kyoto-u.ac.jp, thayashi@kuchem.kyoto-u.ac.jp
Fax: +81-75-753-3988
Tel: +81-75-753-3983

Abstract

A palladium-catalyzed intramolecular decarboxylative cyclization of α-aryl-γ-methylidene-δ-valerolactones, followed by olefin isomerization, has been developed to give fused polycyclic aromatic compounds under mild conditions. The process described here can be regarded as a formal decarboxylative allylic arylation without using a pre-formed organometallic nucleophile. The reaction can be conducted on a gram scale and the products thus obtained are further derivatized with ease.

Graphical abstract: Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones

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Article information

DOI
https://doi.org/10.1039/B924416F
Article type
Communication
Submitted
20 Nov 2009
Accepted
21 Jan 2010
First published
04 Feb 2010

Chem. Commun., 2010,46, 1697-1699

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Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones

R. Shintani, T. Tsuji, S. Park and T. Hayashi, Chem. Commun., 2010, 46, 1697 DOI: 10.1039/B924416F

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