Issue 12, 2011
From the journal:

Organic & Biomolecular Chemistry

N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides†

Floris Chevallier,*a   Yury S. Halauko,*b   Christelle Pecceu,a   Ibrahim F. Nassar,a   To Uyen Dam,a   Thierry Roisnel,c   Vadim E. Matulis,d   Oleg A. Ivashkevichd  and  Florence Mongin*a  

* Corresponding authors

a Chimie et Photonique Moléculaires, UMR 6510 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, Rennes, France
E-mail: floris.chevallier@univ-rennes1.fr, florence.mongin@univ-rennes1.fr
Fax: +33-2-2323-6955

b Department of Electrochemistry of Belarusian State University, 14 Leningradskaya Str., Minsk, Belarus
E-mail: hys@tut.by, halauko@bsu.by

c Centre de Diffractométrie X, Sciences Chimiques de Rennes, UMR 6226 CNRS, Université de Rennes 1, Bâtiment 10B, Case 1003, Campus Scientifique de Beaulieu, Rennes, France

d Research Institute for Physico-Chemical Problems of Belarusian State University, 14 Leningradskaya Str., Minsk, Belarus
Fax: +375-17-2264696

Abstract

A series of N-aryl and N-heteroaryl pyrazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based mixed lithium–zinc combination. Mono-, di-, and tri-iodides have been obtained after subsequent trapping with iodine, depending on the substrate and on the quantity of base used. The results have been discussed in the light of the CH acidities of the substrates, determined both in the gas phase and in THF solution using the DFT B3LYP method.

Graphical abstract: N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides

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Article information

DOI
https://doi.org/10.1039/C1OB05267E
Article type
Paper
Submitted
18 Feb 2011
Accepted
23 Mar 2011
First published
23 Mar 2011

Org. Biomol. Chem., 2011,9, 4671-4684

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N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides

F. Chevallier, Y. S. Halauko, C. Pecceu, I. F. Nassar, T. U. Dam, T. Roisnel, V. E. Matulis, O. A. Ivashkevich and F. Mongin, Org. Biomol. Chem., 2011, 9, 4671 DOI: 10.1039/C1OB05267E

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