1478-53-1Relevant articles and documents
Preparation and synthetic application of diethyl 2-oxo-1,1-difluorophosphonates
Tsai, Hou-Jen
, p. 247 - 259 (1997)
Reaction of diethyl(bromodifluoromethyl)phosphonate (EtO)2P(O)CF2Br 1 with activated zinc gave [(diethoxyphosphonyl)difluoromethyl]zinc bromide (EtO)2P(O)CF2ZnBr 2, which was acylated with various acylating agents to afford diethyl 2-oxo-1,1-difluorophosphonates (EtO)2P(O)CF2C(O)R 4 in good yields. Treatment of phosphonates 4 such as diethyl 2-oxo-1,1-difluoropropylphosphonate (EtO)2P(O)CF2C(O)CH3 4a, ethyl difluoro(diethoxyphosphonyl)pyruvate (EtO)2P(O)CF2C(O)CO2Et 4e and N,N-diethyldifluoro(diethoxyphosphonyl)acetamide (EtO)2P(O)CF2C(O)NEt2 4h with Grignard reagents R'MgX provided 1,1-difluoroolefins R′(CH3)C=CF2, R′(CO2Et)C=CF2 and R′(NEt2) C=CF2, respectively.
Automated lineshape analysis of complex NMR spectra for a novel synthetic tetrafluorobisphosphonate, a potential ligand for phosphoglycerate kinase
Blackburn,H?gele,Hottgenroth,Ivory,Jakeman,Spiske
, p. 367 - 372 (2016)
Tetraalkyl 1,1,3,3-tetrafluoro-2,2-dihydroxypropane-1,3-bisphosphonates were prepared. The complex 31P{1H}- and 19F-NMR spectra were analyzed as [[A]2X]2 and related systems. Modern methods of automated spectral analysis using DAISY under WIN-NMR were applied.
Syntheses of ω-hydroxy-α,α-difluoromethylphosphonates by oxacycle ring-opening reactions
Ozouf, Paul,Binot, Gregory,Pommelet, Jean-Claude,Lequeux, Thierry P.
, p. 3747 - 3750 (2004)
(Chemical Equation Presented) Oxacycle ring-opening reactions from a non-HCFC-based source of phosphonodifluoromethyl carbanion 1 are reported. This straightforward strategy opens access to a variety of primary and secondary ω-hydroxy-α,α-difluoromethylphosphonates via one step. The syntheses of a glycerol monophosphate analogue and precursors to nucleoside phosphorylase inhibitors are described using this method.
Copper-promoted cross-coupling reactions for the synthesis of aryl(difluoromethyl)phosphonates using trimethylsilyl(difluoromethyl)phosphonate
Komoda, Kazuki,Iwamoto, Rei,Kasumi, Masakazu,Amii, Hideki
, (2018)
A convenient and effective route for the synthesis of aryl(difluoromethyl)phosphonates has been developed based on cross-coupling reactions. Upon treatment with a stoichiometric amount (or a catalytic amount in some cases) of CuI and CsF, aryl iodides reacted smoothly with (silyldifluoromethyl)phosphonates to give the corresponding aryl(difluoromethyl)phosphonates in good yields.
Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessinggem-P-containing methanes
Touqeer, Saad,Ielo, Laura,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 2425 - 2429 (2021/04/02)
The direct transfer of different α-substituted methyllithium reagents to chlorinated phosphorous electrophiles of diverse oxidation state (phosphates, phosphine oxides and phosphines) is proposed as an effective strategy to synthesize geminal P-containing
Copper-Mediated Introduction of the CF2PO(OEt)2 Motif: Scope and Limitations
Ivanova, Maria V.,Bayle, Alexandre,Besset, Tatiana,Pannecoucke, Xavier,Poisson, Thomas
, p. 17318 - 17338 (2017/11/20)
Herein, a general procedure to access CF2PO(OEt)2-containing molecules is reported. The reagent CuCF2PO(OEt)2 is accessible by a simple protocol and a broad range of substrates can be functionalised. The procedure allows the conversion of aryl diazonium salts, as well as aryl, heteroaryl, vinyl and alkynyl iodonium salts, into the corresponding fluorinated molecules at room temperature. Mechanistic studies were performed to gain a better understanding of the reaction pathway. Under similar conditions, vinyl and aryl iodides, allyl halides, and benzyl bromides were also functionalised, and the scope and limitations of the reaction were studied. Finally, the procedure was extended to disulfides to offer new access to SCF2PO(OEt)2-containing molecules.
