Issue 30, 2010
From the journal:

Chemical Communications

Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO†

Célia Brancour,a   Takahide Fukuyama,*b   Yuko Ohta,b   Ilhyong Ryu,*b   Anne-Lise Dhimane,a   Louis Fensterbank*a  and  Max Malacria*a  

* Corresponding authors

a Institut Parisien de Chimie Moléculaire (UMR CNRS 7201) - FR 2769 UPMC univ Paris 06, C. 229, 4 place Jussieu, 75005 Paris, France

b Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
E-mail: fukuyama@c.s.osakafu-u.ac.jp
Fax: +82-72-254-9695
Tel: +82-72-254-9743

Abstract

A novel [5+1] type carbonylative cycloaddition reaction has been developed using a Rh complex as catalyst. This reaction can convert readily available 3-acyloxy-1,4-enynes and CO to a wide range of functionalized resorcinols in good yields. A mechanism involving Rh-catalyzed cyclocarbonylation of 3-acyloxy-1,4-enynes accompanied by a 1,2-acyloxy shift is proposed for the present [5+1] type cycloaddition reaction.

Graphical abstract: Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO

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Article information

DOI
https://doi.org/10.1039/C0CC00747A
Article type
Communication
Submitted
03 Apr 2010
Accepted
08 Jun 2010
First published
29 Jun 2010

Chem. Commun., 2010,46, 5470-5472

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Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO

C. Brancour, T. Fukuyama, Y. Ohta, I. Ryu, A. Dhimane, L. Fensterbank and M. Malacria, Chem. Commun., 2010, 46, 5470 DOI: 10.1039/C0CC00747A

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