64196-48-1Relevant academic research and scientific papers
Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones
Maciás-Benítez, Pablo,Sierra-Padilla, Alfonso,Tenorio, Manuel J.,Moreno-Dorado, F. Javier,Guerra, Francisco M.
, p. 16409 - 16424 (2021/11/16)
Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.
Copper ferrite nanoparticles catalyzed formation of β-Ketophosphonates via oxyphosphorylation of styrenes with H-phosphonates: A DFT study on UV–vis absorption spectra
Azaryan, Reza,Daneshfar, Maryam,Moghaddam, Firouz Matloubi,Pirat, Jean-Luc
, (2020/04/21)
Typical copper ferrite nanoparticles (CuFe2O4) were used as a catalyst for one-pot synthesis of β-ketophosphonates via the reaction of alkenes with H-phosphonates under conventional heating conditions. The catalyst was prepared by using the coprecipitation method and was analyzed by physiochemical techniques. By using this catalyst system, several types of useful and new β-ketophosphonate products were obtained in very good to excellent yields under optimized reaction conditions in a novel way. Furthermore, the catalyst is recyclable and reusable from the reaction.
A process for preparing β - carbonyl phosphine ester method
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Paragraph 0072; 0073; 0074; 0075; 0076; 0077, (2017/07/31)
The invention discloses a method for synthesizing beta-carboxyl phosphate from alkyne or alkynyl carboxylic compounds and phosphite ester in the presence of copper/iron salt serving as catalysts and molecular oxygen serving as an oxidant. According to the method, multifunctional beta-carboxyl phosphate is obtained by virtue of a novel method having wide substrate range in the presence of the inexpensive catalysts (copper salts and iron salts) in oxygen, which is in a sharp contrast with previously reported view that alkyne cannot act in the presence of molecular oxygen. The method disclosed by the invention has the advantages of mild reaction conditions, easily available raw materials, good compatibility with various reactants, strong practicality and high yield and can be widely applied to various functional reactions.
Synthesis of α-arylphosphonates using copper-catalyzed α-arylation and deacylative α-arylation of β-ketophosphonates
Rout, Laxmidhar,Regati, Sridhar,Zhao, Cong-Gui
experimental part, p. 3340 - 3346 (2012/01/17)
Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts have been developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data. Copyright
A NEW ONE-POT SYNTHESIS OF β-KETOPHOSPHONATES
Baccolini, Graziano,Todesco, Paolo E.,Dalpozzo, Renato,Nino, Antonio de
, p. 271 - 274 (2007/10/03)
A new synthetic method for the preparation of β-ketophosphonates starting either from azoalkenes and PCl3 or from ketone hydrazones and PCl5 is reported.The reaction involves the addition of alcohols to a diazaphosphole intermediate.This synthesis allows
Lanthanoid-metal-mediated reaction of acylphosphonates: evidence for the formation of an acyllanthanoid complex
Taniguchi, Yuki,Fujii, Nobuto,Takaki, Ken,Fujiwara, Yuzo
, p. 173 - 180 (2007/10/02)
The reactions of diethyl acylphosphonates (1a-e) with Yb and Sm were examined.Reactivities of Yb to 1a-e are different from those of Li and Na.Typically, ethyl benzoylphosphonate (1a) reacts with Yb metal in tetrahydrofuran-hexamethylphosphoramide to afford diethyl 1,2-diphenyl-2-oxoethyl phosphate (2a) and diethyl 1-(diethyl-phosphoryloxy)-1-phenylmethylphosphonate (3a) The formations of 2a and 3a were explained best by the formation of acylytterbium complexes.Keywords: Ytterbium; Samarium; Acylphosphonate; Phosphorus
Reactions of Ethyl phosphites with β-Nitrostyrenes. The Role of Nitrosoalkenes as Intermediates
Russell, Glen A.,Yao, Ching-Fa
, p. 6508 - 6513 (2007/10/02)
3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C while reaction with (EtO)2PO(1-)/(Et2O)P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type aducts are postulated as intermediates.Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C or (EtO)2PO(1-)/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nucleophile at the benzylidene carbonatom.Evidence for the formation of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO(1-)/(EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P.The Michael-type adducts PhCHCH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100 deg C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85percent H2SO4 of the adducts of PhCH=C(R)NO2 with (EtO)2PO(1-) (R = Me) or (EtO)3P (R = Ph).
Synthesis of Phosphonates from α-Hydroxy Carbonyl Compounds and Dialkyl Phosphorochloridites
Roussis, Vassilios,Wiemer, David F.
, p. 627 - 631 (2007/10/02)
In the presence of a Lewis acid, dialkyl phosphorochloridites react with α-hydroxy ketones to afford β-keto phosphonates and with α-hydroxy esters to afford phosphonic acid diesters.These reactions provide convenient access to a variety of structures, inc
La reaction de Wittig-Horner a partir de phosphonate benzylique permet-elle la synthese de stilbene cis ?
Bottin-Strzalko, Tekla,Seyden-Penne, Jacqueline
, p. 161 - 163 (2007/10/02)
The reaction of benzylic phosphonate 2 (Ar = Ph, R = Et) with benzaldehyde gives only trans stilbene whatever the reaction conditions.The base induced decomposition of the two diastereoisomeric hydroxyphosphonates 4 and 5 (Ar = Ar' = Ph, R = Et) precursors of trans or cis stilbene shows that only the former leads to the corresponding olefin; the latter never gives the cis isomer.
