Nucleophilic substitution of pentafluorobenzes with imidazole

Syntheses and structures of N-polyfluorophenyl- and N,N′-bis(polyfluorophenyl)ethane-1,2-diaminato(1- or 2-)platinum(II) complexes

“…The substituent positions for the major and minor components are in good agreement with those of the major and minor products in nucleophilic substitution by methoxide ions in 2-bromo-1,3,4,5-tetrafluorobenzene [34]. By contrast, nucleophilic substitution by imidazole was found to be regiospecific ortho to bromine and para to hydrogen [35], as in the major product of the present syntheses, 3b. Evidently, the stabilisation of the transition state by four electron withdrawing substituents (BrF 3 ) is sufficient to overcome the steric effect of a Br ortho to the point of attack.…”

Pentafluorobenzaldehyde and its utilizing in organic synthesis

“…Imidazole is known to be a weak base, with lower reactivity towards arylhalides than other amines, however, in the imidazole substitution of pentafluorobenzaldehyde, the replacement of the fluorine in p-position proceeds in yield 84% (Scheme 12 [191]). …”

Synthesis and spectroscopy of anionic tridentate benzimidazole-pyridine carboxylate and tetrazolate chromophore ligands

“…This reaction takes advantage of the high reactivity of C-F bond in electron-deficient arenes [40][41][42]. An attempt to make carboxylate ligand 'HL8' from 4 worked for the first three steps (see the intermediates L8-NO 2 , L8-CH 2 OH, L8-CHO and the structure of ligand 'HL8' in the Supplementary material); however, oxidation of the carboxaldehyde L8-CHO to the carboxylic acid 'HL8' with H 2 O 2 in formic acid [26] resulted in oxidative decomposition, probably because of the presence of electron-rich diphenylamino group (Supplementary material).…”