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

作者：Chevallier Floris^*; Halauko Yury S; Pecceu Christelle; Nassar Ibrahim F; Dam To Uyen; Roisnel Thierry; Matulis Vadim E; Ivashkevich Oleg A; Mongin Florence

来源：Organic and Biomolecular Chemistry, 2011, 9(12): 4671-4684.

DOI：10.1039/c1ob05267e

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.

• 出版日期2011