Accessing novel fluorinated heterocycles with the hypervalent fluoroiodane reagent by solution and mechanochemical synthesis
William A. Riley, Andrew C. Jones, Kuldip Singh, Duncan L. Browne, Alison M. Stuart
Abstract
A new and efficient strategy for the rapid formation of novel fluorinated tetrahydropyridazines and dihydrooxazines has been developed by fluorocyclisation of β,γ-unsaturated hydrazones and oximes with the fluoroiodane reagent. Mechanochemical synthesis delivered fluorinated tetrahydropyridazines in similar excellent yields to conventional solution synthesis, whereas fluorinated dihydrooxazines were prepared in much better yields by ball-milling.
Topics & Concepts
Hypervalent moleculeReagentChemistryCombinatorial chemistryFluorineOrganic chemistryFluorine in Organic ChemistryChemical Synthesis and AnalysisSynthesis and Biological Evaluation