N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amidesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra and Cartesian coordinates of molecular geometries for the most stable rotamer forms of studied pyrazoles. CCDC reference numbers 800823-800832, 813448, 813449. For ESI and crystallographic data in CIF or other electronic format see 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. N -(hetero)arylpyrazoles were deproto-metallated using 1 : 1 LiTMP-(TMP) 2 Zn. The reaction outcomes and DFT-calculated CH acidities are discussed.