Synthetic application of fluorinated vinamidinium salts: Synthesis of fluorinated 1,3-butadienylphosphonates by the reaction with Horner-Wadsworth-Emmons reagents |
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| Authors: | Satoru Arimitsu John T Gupton Hiroki Yamanaka |
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| Institution: | a Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan
b Department of Chemistry, University of Richmond, Richmond, VA 23173, USA |
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| Abstract: | The reaction of β-fluoro vinamidinium salt 1 with Horner-Wadsworth-Emmons reagents (HWE) such as diethyl(ethoxycarbonyl)methylphosphonate (2a), diethyl(methoxycarbonyl)methylphosphonate (2b), diethyl-2-oxopropylphosphonate (2c), diethyl benzylphosphonate (2d), tetraethyl methylenediphosphonate (2e) and diethyl cyanomethylphosphonate (2f) under basic conditions gave the fluorinated 1,3-butadienylphosphonates 3 in moderate to good yields. The phosphonates 3 could be hydrolyzed with a 10% HCl aqueous solution to afford the corresponding γ-(diethylphosphono)-α-fluoro-α,β-unsaturated aldehydes 7 in good yields. The treatment of the phosphonate 3c with an NH3 aqueous solution at 70 °C produced the pyridine derivative 8 in 60% yield. |
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| Keywords: | Fluorinated vinamidinium salt Horner-Wadsworth-Emmons reagents Fluorinated 1 3-butadienylphosphonates γ-(Diethylphosphono)-α-fluoro-α β-unsaturated aldehydes Phosphonated pyridine |
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