2959-75-3Relevant academic research and scientific papers
Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium
Zhang, Jian-Qiu,Ikawa, Eiichi,Fujino, Hiroyoshi,Naganawa, Yuki,Nakajima, Yumiko,Han, Li-Biao
, p. 14166 - 14173 (2020/11/13)
Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.
Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds
Li, Chunya,Wang, Qi,Zhang, Jian-Qiu,Ye, Jingjing,Xie, Ju,Xu, Qing,Han, Li-Biao
supporting information, p. 2916 - 2922 (2019/06/18)
Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.
Preparation method of alkyl phosphorylated substances
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Paragraph 0023, (2019/10/04)
The invention discloses a preparation method of alkyl phosphorylated substances. According to the invention, alkyl carboxylic acid is used as a starting material, and raw materials are easy to obtain and are various in types. Products prepared by the method disclosed by the invention are various in types and wide in application; and a part of the products can be prepared into important phosphorus ligands and drug key intermediates through simple reduction. In addition, use of high-toxicity phosphine reagents is avoided in the method, the reaction conditions are mild, operation is simple, the yield of the target product is high, pollution is small, and the reaction operation and post-treatment processes are simple, so that the method is suitable for industrial production.
Dearylation of arylphosphine oxides using a sodium hydride-iodide composite
Tejo, Ciputra,Pang, Jia Hao,Ong, Derek Yiren,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 1782 - 1785 (2018/02/21)
A new protocol for the dearylation of arylphosphine oxides was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The transient sodium phosphinite could be functionalized with a range of electrophiles in a one-pot fashion.
Iridium(III)-Catalyzed C H Amidation of Arylphosphoryls Leading to a P-Stereogenic Center
Gwon, Donghyeon,Lee, Donggun,Kim, Jiyu,Park, Sehoon,Chang, Sukbok
supporting information, p. 12421 - 12425 (2016/08/25)
Direct C H amidation of arylphosphoryl compounds has been developed by using an IrIIIcatalyst system under mild conditions. A wide range of substrates could be employed with high functional-group tolerance. This procedure was successfully applied for the first time to the asymmetric reaction giving rise to a P-chirogenic center with a high diastereomeric ratio of up to 19:1 (90 % de).
METAL-COMPLEX CATALYSIS IN ORGANIC ELECTROSYNTHESIS. I. COUPLING REACTIONS OF COMPOUNDS WITH CARBON-HALOGEN BONDS AND ELEMENT-HALOGEN UNDER THE ACTION OF Ni(0) COMPLEXES
Budnikova, Yu. G.,Kargin, Yu. M.,Novoselova, T. R.
, p. 914 - 916 (2007/10/02)
The possibility was demonstrated for cross-coupling reaction to occur with compounds containing C-Hlg and E-Hlg bonds (Hlg = Br, I; E = H, Si) under the action of electrochemically generated Ni(0) complexes with triphenylphosphine and 2,2'-bipyridyl as ligands.In fact, the metal complex operates as a carrier of the functional group, thus effecting the replacement of halogen in the C-Hlg bonds by organometallic fragments.
Novel Direct Deoxygenation of the Hydroxy Group of (1-Hydroxyalkyl)-diphenylphosphine Oxides
Yamashita, Mitsuji,Suzuki, Takanobu,Imoto, Hiroyuki,Oshikawa, Tatsuo,Inokawa, Saburo
, p. 556 - 557 (2007/10/02)
The hydroxyl group of (1-hydroxyalkyl)-diphenylphosphine oxides 1 is directly deoxygenated on treatment with phosphorus trichloride and iodides to give parent alkyl-diphenylphosphine oxides 2.
Promotion of Dehydrazination by Nitrobenzensulfonyl Group from Phosphorus-hydrazone Adducts
Yamashita, Mitsuji,Takeuchi, Jun,Nakatani, Kaname,Oshikawa, Tatsuo,Inokawa, Saburo
, p. 377 - 378 (2007/10/02)
Dehydrazination of adducts of phenylsulfonylhydrazones and phosphorus compounds was promoted by a nitro substituent on the ring to afford derivatives of a phosphine oxide and phosphonates.
Nucleophilic Substitution with Phosphide Anions Prepared by an Action of Sodium Dihydridobis(2-methoxyethanolato)aluminate on Phosphorus Compounds
Yamashita, Mitsuji,Suzuki, Nobuyoshi,Yamada, Manabu,Soeda, Yukio,Yamashita, Hiroaki,et al.
, p. 219 - 222 (2007/10/02)
Phosphide anions, prepared by an action of sodium dihydridobis(2-methoxyethanolato)aluminate on derivatives of phosphine, phosphine oxide, or phosphorus esters, react with primary and secondary alkyl halides to produce phosphine derivatives having a newly formed phosphorus-carbon bond.The reactivity increases in the order of chloride N2 type process.
