An improved preparation of α-fluorinated propargylphosphonates and the solid phase synthesis of α-hydroxy-γ-TIPS propargylphosphonate ester

Diethyl-3-triisopropylsilyl-1-propynephosphonate was fluorinated using NFSI to give the corresponding monofluoroderivative in good yield. The synthesis of diethyl-1,1-difluoro-3-triisopropylsilylpropynephosphonate was efficiently achieved following Burton’s methodology using CuCl/Cd to promote the coupling reaction of diethyl bromodifluoromethylphosphonate with the corresponding alkynyl iodide. Although the solid phase synthesis of α-hydroxy-γ-TIPS propargylphosphonate ester was carried out successfully, its fluorination — using DAST — failed.