Issue 8, 2010
From the journal:

Physical Chemistry Chemical Physics

A theoretical study of the copper(i)-catalyzed 1,3-dipolar cycloaddition reaction in dabco-based ionic liquids: the anion effect on regioselectivity†

Cinzia Chiappe,a   Benedetta Mennucci,a   Christian Silvio Pomelli,*a   Angelo Sanzonea  and  Alberto Marrab  

* Corresponding authors

a Dipartimento di Chimica e Chimica Industriale, via Risorgimento 35, 56126 Pisa, Italy

b Dipartimento di Chimica, Laboratorio di Chimica Organica, via L. Borsari 46, 44100 Ferrara, Italy

Abstract

The regioselectivity of copper(I)-catalyzed synthesis of 1,2,3-triazoles in dabco-based ionic liquids has been investigated at the DFT level using a supermolecular approach. The analysis of the theoretical results shows that the coordination ability of the ionic liquid (IL) anion to copper(I) catalyst and to all the other species containing the copper (intermediates and transition states) can significantly affect product distribution. Possible catalyst sequestering effects and the ability to stabilize selectively new intermediate species have been envisaged, as probable mechanisms throughout IL anions can affect copper catalyzed reactions inside performed.

Graphical abstract: A theoretical study of the copper(i)-catalyzed 1,3-dipolar cycloaddition reaction in dabco-based ionic liquids: the anion effect on regioselectivity

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Article information

DOI
https://doi.org/10.1039/B921204C
Article type
Paper
Submitted
14 Oct 2009
Accepted
12 Jan 2010
First published
21 Jan 2010

Phys. Chem. Chem. Phys., 2010,12, 1958-1962

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A theoretical study of the copper(I)-catalyzed 1,3-dipolar cycloaddition reaction in dabco-based ionic liquids: the anion effect on regioselectivity

C. Chiappe, B. Mennucci, C. Silvio Pomelli, A. Sanzone and A. Marra, Phys. Chem. Chem. Phys., 2010, 12, 1958 DOI: 10.1039/B921204C

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