Article

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

Chimie et Photonique Moléculaires, UMR 6510 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042, Rennes, France.
Organic & Biomolecular Chemistry (impact factor: 3.7). 04/2011; 9(12):4671-84. DOI:10.1039/c1ob05267e pp.4671-84
Source: PubMed

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.

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Keywords

2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination
 
CH acidities
 
gas phase
 
iodine
 
N-aryl
 
THF solution
 
tri-iodides
 

Floris Chevallier