3049-24-9Relevant academic research and scientific papers
Direct18F-Labeling of Biomolecules via Spontaneous Site-Specific Nucleophilic Substitution by F-on Phosphonate Prostheses
Wang, Chao,Zhang, Lei,Mou, Zhaobiao,Feng, Wanru,Li, Zhongjing,Yang, Hongzhang,Chen, Xueyuan,Lv, Shengji,Li, Zijing
supporting information, p. 4261 - 4266 (2021/05/26)
We describe a high radiochemical yield late-stage direct 18F-labeling of bare biomolecules containing common active groups. Spontaneity and site-selectivity are attributed to the remarkably higher rates of nucleophilic substitution reactions on phosphonates than on other electrophiles by F- at various hydrogen bond forms. Rapid access to many medicinally significant 18F-labeled biomolecules is achieved at 21-68% radiochemical yields and 35.9-55.1 GBq μmol-1 molar activities both manually or automatically.
Preparation method of phenyl phosphonate diphenyl ester (by machine translation)
-
Paragraph 0045-0052; 0057-0085; 0093-0096, (2020/09/16)
The invention belongs to the technical field of organic synthesis, and provides a preparation method of diphenyl phosphonate, wherein triphenyl phosphite is used as an initiator, and the molar ratio ?timetime? and isomerization reaction is controlled to obtain phenyl phosphonate diphenyl ester; the isomerization reaction temperature is 220 - 260 °C. the isomerization reaction temperature is controlled; 1st. In addition, both the brominated benzene and Raney nickel in the method can be recycled, the reaction cost is low, and the environmental pollution is small. (by machine translation)
Palladium-catalyzed solvent-free preparation of arylphosphonates Arp(O)(OAr)2 from (Aro)3p via the Michaelis-Arbuzov rearrangement
Li, Chunya,Han, Li-Biao
supporting information, p. 3613 - 3617 (2020/11/03)
The Pd-catalyzed Michaelis-Arbuzov rearrangement of triaryl phosphites to produce the corresponding arylphosphonates in good to excellent yields is disclosed. In comparison to the traditional methods, this new method is highly atom efficient and is general, as it can be readily extended to aryl phosphonites and phosphinites. A gram-scale reaction of (PhO)3P to PhP(O)(OPh)2 with low loading of the catalyst was also demonstrated to show its potentially practical usefulness. A plausible mechanism is proposed.
Synthesis of New Chiral Crown Ethers Containing Phosphine or Secondary Phosphine Oxide Units
Szabó-Szentjóbi, Hajnalka,Majoros, István,Márton, Anna,Leveles, Ibolya,Vértessy, Beáta G.,Dékány, Miklós,Tóth, Tünde,Huszthy, Péter
, p. 2870 - 2882 (2020/10/06)
The transition-metal complexes of phosphine and secondary phosphine oxide compounds can be used in various catalytic reactions. In this paper, the synthesis and characterization of eight new crown ethers containing trivalent phosphorus in their macroring are reported. These macrocycles are promising candidates as ligands for catalytic reactions.
Cobalt catalyzed C-P bond formation by cross-coupling of boronic acids with P(O)H compounds in presence of zinc
Hicks, Ian,McTague, Jonathan,Hapatsha, Tatiana,Teriak, Rania,Kaur, Parminder
, (2020/01/31)
In our current work, we have reported the first cobalt-catalyzed cross-coupling of arylboronic acid with alkyl/aryl phosphites under mild conditions. The reaction was carried out in the presence of zinc powder as an additive and ter-pyridine as a ligand. The use of non-precious cobalt salt makes the protocol advantageous, as it is inexpensive and more abundant than the previously used methods where precious metal salts (Pd and Pt) were used. The reaction has a wide substrate scope and the products were obtained in good yields.
Radical arylation of triphenyl phosphite catalyzed by salicylic acid: Mechanistic investigations and synthetic applications
Estruch-Blasco, Manel,Felipe-Blanco, Diego,Bosque, Irene,Gonzalez-Gomez, Jose C.
supporting information, p. 14473 - 14485 (2020/12/29)
A straightforward and scalable methodology to synthesize diphenyl arylphosphonates at 20 °C within 1-2 h is reported using inexpensive SA as the catalytic promoter of the reaction. Mechanistic investigations suggest that the reaction proceeds via radical-radical coupling, consistent with the so-called persistent radical effect. The reaction tolerated a wide range of functional groups and heteroaromatic moieties. The synthetic usefulness and the unique reactivity of the obtained phosphonates were demonstrated in different one-step transformations.
Visible Light-Driven, Photocatalyst-Free Arbuzov-Like Reaction via Arylazo Sulfones
Qiu, Di,Lian, Chang,Mao, Jinshan,Ding, Yi,Liu, Zerong,Wei, Liyan,Fagnoni, Maurizio,Protti, Stefano
supporting information, p. 5239 - 5244 (2019/11/11)
A visible light-induced formation of Aryl-Phosphorous bonds starting from arylazo sulfones and triaryl (or trialkyl)phosphites in the absence of any photoredox catalyst and any additives was developed. This reaction showed a broad substrate scope and afforded (hetero)aryl phosphonates in good yields and in up to the gram scale.
Arylphosphate compound and preparation method thereof
-
Paragraph 0011; 0014; 0020, (2019/04/17)
The invention discloses an arylphosphate compound and a preparation method thereof. The preparation method includes, with arylamine and phosphite ester as reactants and tert-butyl nitrite as an accelerator, performing stirring reaction at the temperature within 70-80 DEG C for 40-60 minutes, and separating through the column chromatography to obtain a product, namely arylphosphate compound. The preparation method is a new way of synthetizing arylphosphate target compound from low-price feasible raw materials of arylamine and phosphite ester on the acid-free and metal-free condition, has the advantages of mild reaction condition, operational simplicity and the like and overcomes the big trouble to production of medical intermediates caused by residues of metal catalysts, after-treatment ofacids in medicine synthesis, and accordingly, the simple and efficient meta-free and acid-free catalysis system has great potential application value and economic benefit.
Avisible-light-promoted metal-free strategy towards arylphosphonates: Organic-dye-catalyzed phosphorylation of arylhydrazines with trialkylphosphites
Li, Rui,Chen, Xiaolan,Wei, Shengkai,Sun, Kai,Fan, Lulu,Liu, Yan,Qu, Lingbo,Zhao, Yufen,Yu, Bing
supporting information, p. 4807 - 4813 (2018/12/11)
A visible-light-induced metal-free catalytic system was developed for the synthesis of arylphosphonates starting from arylhydrazines and trialkylphosphites. By using the inexpensive eosin B as catalyst, sub-stoichiometric amounts of DABCO, and ambient air as oxidant, diverse arylphosphonates were obtained under visible-light irradiation. Notably, this catalytic system is suitable for gram-scale reaction by utilizing sunlight as an illumination source.
Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations
Lecroq, William,Bazille, Pierre,Morlet-Savary, Fabrice,Breugst, Martin,Lalevée, Jacques,Gaumont, Annie-Claude,Lakhdar, Sami
supporting information, p. 4164 - 4167 (2018/07/29)
This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.
