Fluorinated Phoshonates as Reagents for the Introduction of Fluorinated Functional Groups

Authors

  • P. Beier Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague
  • S. Opekar Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague

Keywords:

phosphonate, fluorine, nucleophilic addition, fluoralkylation, elimination, rearrangement, conjugate addition, dissociation constant, C-H acids

Abstract

This review introduces α-fluorophosphonates as useful synthons and fluoroalkyl transfer reagents. The remarkable biological activity of the phosphonates is also mentioned. The main emphasis is put on synthetic applications of the following fluorinated phosphonates: diethyl (difluoromethyl)phosphonate (1), diethyl (trifluoromethyl)phosphonate (2), tetraethyl (fluoromethylene)bis­phosphonate (3), diethyl  [(fluoromethyl) (phenylsulfonyl)methyl]phosphonate (McCathy's reagent) (4), and diethyl (fluoronitromethyl)phosphonate (5). The review is focused on the chemistry of the synthons.

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Published

2014-10-15

How to Cite

Beier, P., & Opekar, S. (2014). Fluorinated Phoshonates as Reagents for the Introduction of Fluorinated Functional Groups. Chemické Listy, 108(10), 926–936. Retrieved from http://ww-w.chemicke-listy.cz/ojs3/index.php/chemicke-listy/article/view/446

Issue

Vol. 108 No. 10 (2014)

Section

Articles