Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 15, Pages 11258-11262Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00396
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A facile one-pot (3 + 2) cycloaddition-isomerization-oxidation sequence using 2,2,2-trifluorodiazoethane and styryl derivatives has been developed for the synthesis of 5-aryl-3-trifluoromethylpyrazoles. The reaction showed broad functional group tolerance and high yields under mild conditions. DFT calculations confirmed the reactivity observed experimentally by analyzing the transition state energies of the cycloaddition reaction.
A facile access to5-aryl-3-trifluoromethylpyrazoles has been developedby a one-pot (3 + 2) cycloaddition-isomerization-oxidationsequence employing 2,2,2-trifluorodiazoethane and styryl derivatives.A broad variety of functional groups and good yields are achievedunder mild conditions. Additionally, the functionalization of 3-trifluoromethylpyrazoleswas studied. DFT calculations of the cycloaddition transition stateenergies are consistent with the experimentally observed reactivity.
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