One-Pot (3 + 2) Cycloaddition–Isomerization–Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives
Julia Altarejos, Estı́baliz Merino, David Sucunza, Juan J. Vaquero, Javier Carreras
Abstract
A facile access to 5-aryl-3-trifluoromethylpyrazoles has been developed by a one-pot (3 + 2) cycloaddition-isomerization-oxidation sequence employing 2,2,2-trifluorodiazoethane and styryl derivatives. A broad variety of functional groups and good yields are achieved under mild conditions. Additionally, the functionalization of 3-trifluoromethylpyrazoles was studied. DFT calculations of the cycloaddition transition state energies are consistent with the experimentally observed reactivity.
Topics & Concepts
CycloadditionIsomerizationReactivity (psychology)ChemistrySequence (biology)PhotochemistrySurface modificationArylComputational chemistryCombinatorial chemistryCatalysisOrganic chemistryPhysical chemistryMedicineAlkylAlternative medicinePathologyBiochemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Biological Evaluation