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Metallacycle-Catalyzed S N Ar Reaction in Water: Supramolecular Inhibition by Means of Host–Guest Complexation

2014; American Chemical Society; Volume: 79; Issue: 3 Linguagem: Inglês

10.1021/jo402689p

1520-6904

Eva M. López‐Vidal, Antonio Fernández‐Mato, Marcos D. García, Moisés Pérez‐Lorenzo, Carlos Peinador, José M. Quintela,

Chemical Reaction Mechanisms

The performance of a Pt(II) diazapyrenium-based metallacycle as a reusable substoichiometric catalyst for the SNAr reaction between halodinitrobenzenes and sodium azide at rt in aqueous media is reported. The results suggest that the catalytic effect is promoted by the association of the azide to the diazapyrenium cationic subunits of the catalyst. The findings demonstrate that the formation of an inclusion complex between pyrene and the metallacycle has a regulatory effect over the system, resulting in allosteric-like inhibition of the SNAr reaction.