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Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods.

Walid Fathalla1, Ibrahim A I Ali2, Pavel Pazdera3

  • 1Physics and Math. Engineering Dept., Faculty of Engineering, Port-Said University Port Said Egypt walid3369@yahoo.com.

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|May 11, 2022
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Summary

Researchers developed efficient methods for synthesizing ether phosphonates using trichloroacetimidate and acetate coupling. This C-O bond formation technique yields 21 diverse phosphonate compounds with high efficiency and speed.

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Area of Science:

  • Organic Chemistry
  • Organophosphorus Chemistry

Background:

  • Ether phosphonates are valuable compounds with diverse applications.
  • Efficient synthetic routes are crucial for accessing novel organophosphorus compounds.

Purpose of the Study:

  • To develop novel and efficient synthetic methodologies for ether phosphonates.
  • To prepare a library of diethyl alkyloxy(substitutedphenyl)methyl phosphonates.

Main Methods:

  • Utilized trichloroacetimidate and acetate coupling reactions.
  • Employed primary and secondary alcohols as O-nucleophiles.
  • Catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf) were used.

Main Results:

  • Successfully synthesized 21 examples of diethyl alkyloxy(substitutedphenyl)methyl phosphonates.
  • Achieved C-O bond formation with yields ranging from 55-90%.
  • Demonstrated short reaction times for the coupling methods.

Conclusions:

  • The developed trichloroacetimidate and acetate coupling methods are effective for ether phosphonate synthesis.
  • These methods provide a versatile route to functionalized phosphonate compounds.
  • The study highlights efficient C-O bond formation for organophosphorus synthesis.