773-47-7Relevant academic research and scientific papers
Synthesis of α-Aryldiazophosphonates via a Diazo Transfer Reaction
Beletskaya, Irina P.,Titanyuk, Igor D.
, p. 2748 - 2757 (2022/03/14)
The simple synthetic procedure for preparation of α-aryl-α-diazophosphonates via a diazo transfer reaction is proposed. Benzylphosphonates reacted with tosyl azide (TsN3) in the presence of potassium tert-butoxide (KOtBu) to afford diazophosphonates in a yield up to 79%. The proposed method is general. The reaction uses easily available starting materials, tolerates various functional groups, and may be applied for multi-gram scale synthesis.
Disulfide Promoted C?P Bond Cleavage of Phosphoramide: “P” Surrogates to Synthesize Phosphonates and Phosphinates
Hou, Fei,Du, Xing-Peng,Alduma, Anwar I.,Li, Zhi-Feng,Huo, Cong-De,Wang, Xi-Cun,Wu, Xiao-Feng,Quan, Zheng-Jun
supporting information, p. 4755 - 4760 (2020/10/06)
A metal-free C?P bond cleavage reaction is described herein. Phosphoramides, a phosphine source, can react with alcohols to produce phosphonate and phosphinate derivatives in the presence of a disulfide. P?H2, P-alkyl, and P,P-dialkyl phosphoramides can be used as substrates to obtain the corresponding pentavalent phosphine products. (Figure presented.).
Preparation method of aryl methyl phosphine acylate
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Paragraph 0037, (2019/10/01)
The invention discloses a preparation method of aryl methyl phosphine acylate. The method uses (hetero) aryl acetic acid as the starting material, and the raw materials are easily available and have agreat variety. The product obtained by the method provided by the invention has various types and wide uses. The aryl methyl phosphine acylate can be easily converted into a bis (hetero)arylethene derivative, and the compound can be used for preparation of dyes, fluorescent agents, whiteners, light-emitting diodes and other devices. In addition, the method disclosed by the invention has the advantages of easily available, stable and low toxicity raw materials, mild reaction conditions, high yield of target product, low pollution, simple reaction operation and post-treatment process, and is suitable for industrial production.
Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes
Huang, Tianzeng,Chen, Tieqiao,Han, Li-Biao
, p. 2959 - 2965 (2018/03/09)
Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.
Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation
Ma, Xiantao,Xu, Qing,Li, Huan,Su, Chenliang,Yu, Lei,Zhang, Xu,Cao, Hongen,Han, Li-Biao
supporting information, p. 3408 - 3413 (2018/08/06)
The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.
Synthesis and inhibitory activity of acetamidophosphonic acids against metallo-β-lactamases
Zhang, Yi-Lin,Zhang, Yue-Juan,Wang, Wen-Ming,Yang, Ke-Wu
, p. 14 - 18 (2016/12/24)
Metallo-β-lactamases (MβLs) are the target enzymes of antibiotic resistance and the phosphonic drugs make great influence to the development of contemporary medicine. Eleven acetamidophosphonic compounds were prepared and evaluated as inhibitors of the MβLs. Compounds 4, 5, 7, 9, and 10 exhibited specific inhibitory activity against the MβL NDM-1 and CcrA with an IC50 value range of 17 to 354 μM. Analysis of the structure–activity relationship showed that both the acetamido linker and the position of the substituent on the phenyl ring played an important role in the inhibitory abilities of the inhibitors against MβLs.
Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles
Makida, Yusuke,Usui, Kazumi,Ueno, Satoshi,Kuwano, Ryoichi
, p. 1814 - 1817 (2017/11/23)
A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.
Investigation of reactive intermediates and reaction pathways in the coupling agent mediated phosphonamidation reaction
Fredriksen, Kim Alex,Amedjkouh, Mohamed
supporting information, p. 474 - 482 (2016/02/18)
The preparation of carboxamides through the coupling agent mediated reaction of carboxylic acids and amines is one of the most frequently employed reaction types of modern organic synthesis and has largely replaced older methods of amide formation based on reactive acyl chloride intermediates. However, the preparations of analogous phosphonamidates still rely on the use of phosphonochloridate intermediates - a method that is incompatible with sensitive functional groups. Herein, we present a comprehensive study in which different coupling agents are tested in the phosphonamidation reaction. The procedures, parallel to those typically applied to the preparation of carboxamides, were generally unsuccessful with regard to the coupling reactions of monoesters of phosphonic acids and amines, with the exception of those mediated by (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP). The implementation of a preactivation period in the absence of the amine coupling partner allowed for efficient phosphonamidate formation with coupling agents such as (1-cyano-2-ethyoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (COMU), [ethyl cyano(hydroxyimino)acetato-O2]tri-1-pyrrolidinylphosphonium hexafluorophosphate (PyOxim), dicyclohexyl carbodiimide (DCC), N,N′-diisopropylcarbodiimide (DIC), and N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU). The reactive intermediates observed by 31P NMR analysis were individually synthesized and examined to understand their influence on the reaction. A phosphonamidation reaction that uses (1-cyano-2-ethyoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (COMU) to mediate the coupling of monoalkyl esters of phosphonic acids and amines was developed. A preactivation period without the amine was needed to obtain the product. Using this step allowed for other coupling agents to be successfully used in the reaction.
Recognition characteristics of an adaptive vesicular assembly of amphiphilic baskets for selective detection and mitigation of toxic nerve agents
Chen, Shigui,Ruan, Yian,Brown, Jason D.,Hadad, Christopher M.,Badji, Jovica D.
supporting information, p. 17337 - 17342 (2015/02/02)
We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 ?3) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 ?3) in water at 298.0 K. The encapsulation is, in each case, dri
Palladium(II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates
Meng, Xiangjian,Kim, Sunggak
, p. 11247 - 11254 (2013/12/04)
The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-ary
