83567-77-5Relevant academic research and scientific papers
α,α-Difluoro-β-iminophosphonates, an alternative strategy towards the synthesis of α,α-difluoro-β-aminophosphonate derivatives
Szewczyk,Rapp,Virieux,Pirat,Koroniak
supporting information, p. 6322 - 6333 (2017/07/17)
α,α-Difluoromethylenephosphonates are generally known as stable natural phosphate mimics with significantly improved biological activities. A number of α,α-difluoroalkylphosphonates have already been found to be important enzyme inhibitors. Herein, we report an alternative strategy towards the synthesis of α,α-difluoromethylene-β-aminophosphonate derivatives. A small library of N-substituted α,α-difluoro-β-aminophosphonates was designed and described via NMR study. The protocol began with the condensation of β-ketophosphonates with a series of primary amines. The key step of the synthesis is an electrophilic fluorination, mediated by Selectfluor, of the mixture of β-enamino/β-iminophosphonates leading to α,α-difluoro-β-iminophosphonates followed by reduction. The title compounds may behave as convenient building blocks for further more advanced modification.
Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate
Beier, Petr,Alexandrova, Anastasia V.,Zibinsky, Mikhail,Surya Prakash
experimental part, p. 10977 - 10985 (2009/04/11)
New methodology for difluoromethylation and difluoromethylenation of aldehydes and ketones based on nucleophilic fluorination using diethyl difluoromethylphosphonate (1) was developed.
Reformatsky-type co-mediated synthesis of β-hydroxyphosphonates
Orsini, Fulvia
, p. 1425 - 1428 (2007/10/03)
Low-valent cobalt complexes were used in Reformatsky-type additions of α-halophosphonates to carbonyl compounds (ketones and aldehydes) to yield a variety of β-hydroxyphosphonates.
(DIETHYLPHOSPHINYL)DIFLUOROMETHYLLITHIUM. -PREPARATION AND SYNTHETIC APPLICATION-
Obayashi, Michio,Ito, Eiji,Matsui, Kiyohide,Kondo, Kiyosi
, p. 2323 - 2326 (2007/10/02)
The action of lithium diisopropylamide on diethyl difluoromethylphosphonate gives the title reagent which reacts with various electrophiles to introduce difluoromethylene or difluoromethyl unit.
AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF 1,1-DIFLUORO-2-HYDROXYALKYLPHOSPHONATES
Obayashi, Michio,Kondo, Kiyosi
, p. 2327 - 2328 (2007/10/02)
The reaction of diethyl difluoro(trimethylsilyl)methylphosphonate with arenecarbaldehydes and aryl methyl ketones is effected with the aid of a catalyst, cesium fluoride, at room temperature to afford the title compounds.
