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

Antonio Arcadi, Federico Blesi, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, Fabio Marinelli

Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi di L'Aquila, Via Vetoio, 67010 Coppito, L'Aquila, Italy. antonio.arcadi@univaq.it

Organic & biomolecular chemistry 2012 Dec 28

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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.

Citation

Antonio Arcadi, Federico Blesi, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, Fabio Marinelli. Gold versus silver catalyzed intramolecular hydroarylation reactions of [(3-arylprop-2-ynyl)oxy]benzene derivatives. Organic & biomolecular chemistry. 2012 Dec 28;10(48):9700-8