Issue 23, 2008
From the journal:

Chemical Communications

Palladium(ii)-catalyzed ring enlargement of 2-(arylmethylene)cyclopropylcarbinols: strong effect of substituent electronic nature on the reaction pathway†

Guo-Qiang Tian,a   Zhi-Liang Yuan,b   Zhi-Bin Zhub  and  Min Shi*ab  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China
E-mail: Mshi@mail.sioc.ac.cn

b School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai, China

Abstract

In the presence of Pd(II) catalyst and copper(II) bromide, 2-(arylmethylene)cyclopropylcarbinols undergo ring enlargement to deliver (arylcyclobutenyl)carbinols or hydrogenated furans in good yields under mild conditions; mechanisms accounting for the distinct products have been proposed on the basis of control and deuterium labeling experiments.

Graphical abstract: Palladium(ii)-catalyzed ring enlargement of 2-(arylmethylene)cyclopropylcarbinols: strong effect of substituent electronic nature on the reaction pathway

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Article information

DOI
https://doi.org/10.1039/B804932G
Article type
Communication
Submitted
25 Mar 2008
Accepted
25 Apr 2008
First published
08 May 2008

Chem. Commun., 2008, 2668-2670

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Palladium(II)-catalyzed ring enlargement of 2-(arylmethylene)cyclopropylcarbinols: strong effect of substituent electronic nature on the reaction pathway

G. Tian, Z. Yuan, Z. Zhu and M. Shi, Chem. Commun., 2008, 2668 DOI: 10.1039/B804932G

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