Issue 48, 2012
From the journal:

Organic & Biomolecular Chemistry

Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives†

Antonio Arcadi,*a   Federico Blesi,a   Sandro Cacchi,b   Giancarlo Fabrizi,*b   Antonella Goggiamanib  and  Fabio Marinellia  

* Corresponding authors

a Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L'Aquila, Via Vetoio, 67010 Coppito, L'Aquila, Italy
E-mail: antonio.arcadi@univaq.it
Fax: +390862433033

b Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, Rome, Italy
E-mail: giancarlo.fabrizi@uniroma1.it

Abstract

The scope and the generality of gold versus silver catalyzed intramolecular hydroarylation reactions of 3-[(3-arylprop-2-ynyl)oxy]benzene derivatives in terms of rings substitution were investigated. Only products deriving from 6-endo cyclization were exclusively formed. The features of substituents had a considerable effect on the reaction outcome in the presence of silver catalysis, whereas gold catalysis revealed a unique blend of reactivity and selectivity and represented the only choice for the intramolecular hydroarylation reaction of the starting substrates bearing electron deficient arenes.

Graphical abstract: Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives

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Article information

DOI
https://doi.org/10.1039/C2OB26763B
Article type
Paper
Submitted
07 Sep 2012
Accepted
16 Oct 2012
First published
17 Oct 2012

Org. Biomol. Chem., 2012,10, 9700-9708

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Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives

A. Arcadi, F. Blesi, S. Cacchi, G. Fabrizi, A. Goggiamani and F. Marinelli, Org. Biomol. Chem., 2012, 10, 9700 DOI: 10.1039/C2OB26763B

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