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

The performance of a PtII 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...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2014-02, Vol.79 (3), p.1265-1270
Main Authors: López-Vidal, Eva M, Fernández-Mato, Antonio, García, Marcos D, Pérez-Lorenzo, Moisés, Peinador, Carlos, Quintela, José M
Format: Article
Language:English
Subjects:
Catalysis
Nitrobenzenes - chemical synthesis
Nitrobenzenes - chemistry
Organoplatinum Compounds - chemistry
Pyrenes - chemistry
Water
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The performance of a PtII 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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402689p