7369-51-9Relevant academic research and scientific papers
B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
Jiang, Jun,Zhang, Xinzhi,Zhang, Yangyang,Zhao, Jincheng
, p. 5772 - 5776 (2021/07/12)
A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.
Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
, p. 6007 - 6014 (2021/07/21)
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
Golden Face of Phosphine: Cascade Reaction to Bridgehead Methanophosphocines by Intramolecular Double Hydroarylation
Babouri, Rachida,Traore, Lanciné,Bekro, Yves-Alain,Matveeva, Victoria I.,Sadykova, Yulia M.,Voronina, Julia K.,Burilov, Alexander R.,Ayad, Tahar,Volle, Jean-No?l,Virieux, David,Pirat, Jean-Luc
supporting information, p. 45 - 49 (2019/01/04)
Reported herein is the first example of a gold-catalyzed cyclization of bis(arylmethyl)ethynylphosphine oxides. This represents an original approach to bridgehead methanophosphocines 1, eight-membered heterocycles. Gold catalyst in combination with triflic acid activates alkyne and induces a double hydroarylation. Mechanistic studies suggest that the reaction proceeds stepwise, forming first the 1H-isophosphinoline 2-oxide 5. Reduction and protection of the corresponding phosphine oxides 1 described herein also highlight the effectiveness of our approach to this new class of electron-rich ligands.
Direct, oxidative halogenation of diaryl- or dialkylphosphine oxides with (dihaloiodo)arenes
Eljo, Jasmin,Murphy, Graham K.
supporting information, p. 2965 - 2969 (2018/06/30)
The oxidative halogenation of diaryl- or dialkylphosphine oxides with the hypervalent iodine reagents (difluoroiodo)toluene (p-TolIF2, 1) and (dichloroiodo)benzene (PhICl2, 2) is reported. Phosphoric fluorides could be recovered in 32–75% yield, or they could be trapped with EtOH to give the corresponding phosphinate in typically good yield. Phosphoric chlorides were not readily isolable, and were trapped with alcohol and amine nucleophiles, giving diaryl- or dialkylphos-phinates and phosphinamides in up to 90% yield.
Insertion of Arynes into P-O Bonds: One-Step Simultaneous Construction of C-P and C-O Bonds
Qi, Na,Zhang, Ning,Allu, Srinivasa Rao,Gao, Jiangsheng,Guo, Jian,He, Yun
supporting information, p. 6204 - 6207 (2016/12/09)
The insertion of arynes into P-O bonds for the preparation of o-hydroxy-substituted arylphosphine oxides, -phosphinates, and -phosphonates is described. This novel reaction leads to the simultaneous formation of C-P and C-O bonds in one step with good yie
Electrophilic Fluorination of Secondary Phosphine Oxides and Its Application to P-O Bond Construction
Chen, Qian,Zeng, Jiekun,Yan, Xinxing,Huang, Yulin,Wen, Chunxiao,Liu, Xingguo,Zhang, Kun
, p. 10043 - 10048 (2016/11/02)
A novel and efficient electrophilic fluorination of secondary phosphine oxides with Selectfluor has been achieved. This transformation provides direct access to phosphoric fluorides in up to 92% yield under mild conditions. In addition, P-O bond construction via a one-pot coupling process of secondary phosphine oxides with water or alcohols in the presence of Selectfluor leads to the formation of phosphinic acids or phosphinates in up to 96% yield.
Aluminum-organophosphorus hybrid nanorods for simultaneously enhancing the flame retardancy and mechanical properties of epoxy resin
Jiajun, Ma,Junxiao, Yang,Yawen, Huang,Ke, Cao
, p. 2007 - 2017 (2013/01/15)
New aluminum-organophosphorus hybrid nanorods (AOPH-NR) have been prepared by reacting aluminum hydroxide (ATH) with dibenzylphosphinic acid (DBPA) with aluminum hydroxide (ATH) and used to prepare nanocomposites with epoxy resin. In order to determine the structure-property relationship of these composites, several other phosphinic acids of the general formula (R(CH2) n)2POOH (R = ester, allyl, nitrile, n = 1 or 2), and corresponding AOPHs were synthesized. FTIR, Raman, TGA, and XRD examinations showed that only AOPH-NR possesses a highly hybrid structure and high thermostability. SEM and TEM confirmed the nanorod morphology of AOPH-NR. The formation mechanism can be described as a decomposing-reforming process. This characteristic causes AOPH-NR to exhibit superior properties. Limiting oxygen index (LOI) determination and cone calorimeter analysis showed that the incorporation of only 4.25 wt% AOPH-NR remarkably improved the LOI value to as much as 28.0 and led to a 23% reduction in peak heat release rate (PHRR). Dynamic mechanical analysis (DMA) indicated that the mechanical properties of epoxy resin were also improved by incorporating AOPH-NR. In this way, the aluminum-organophosphorus hybridization via reacting ATH with specific organophosphinic acids shows promise as a means of improving flame retardancy and mechanical properties simultaneously. The thermal and anti-flaming properties of composites, combined with the properties of AOPHs, allowed us to discover the important role that the release and migration of phosphorus species plays in fire-retarding materials. This provides a new insight into the design of high-performance flame retardants.
Direct conversion of secondary phosphine oxides and h-phosphinates with [Di(acyloxy)iodo]benzenes to phosphinic and phosphonic amides
Hubacz, Anna,Makowiec, Slawomir
experimental part, p. 81 - 86 (2009/09/25)
The reaction of [di(acyloxy)iodo]- benzene with secondary phosphine oxides or H-phosphinates in the presence of primary or secondary amines allows one to obtain phosphinic or phosphonic acids amides in the one-pot process. We take advantage of the strong acylating system DAIB/R2P(O)H to phosphinylation of amines. However, the reaction mechanism is multipathway and causes yields of phosphinic or phosphonic acids amides to be moderate. When the concentration of amines is low, the intermolecular process plays a main role leading to the formation of carboxylic amides through mixed phosphoric-carboxylic anhydride, and also in the low concentration of amines, tetrahydrofuran effectively competes with the amines in the nucleophilic attack on the acylating intermediates.
Reactions of elemental phoshorus and phosphine with electrophiles in superbasic systems: XIX. Formation of the C-P bond with participation of elemental phosphorus under microwave assistance
Malysheva,Gusarova,Kuimov,Sukhov,Kudryavtsev,Sinyashin,Budnikova,Pai,Tolstikov,Trofimov
, p. 415 - 420 (2008/02/11)
Microwave irradiation facilitates phosphorylation of aryl methyl chlorides and styrene with red phosphorus in the presence of strong bases and increases the yield of the main products, tertiary phosphine oxides. Nauka/Interperiodica 2007.
Reactions of elemental phosphorus and phosphine with electrophiles in superbasic systems: XVI. Phosphorylation of benzyl chloride with elemental phosphorus and phosphine
Trofimov,Gusarova,Malysheva,Shaikhudinova,Belogorlova,Kazantseva,Sukhov,Plotnikova
, p. 684 - 688 (2007/10/03)
The major product of the reaction of benzyl chloride with red phosphorus in the system concentrated aqueous KOH-dioxane-phase-transfer catalyst (43-95°C, Ar) is tribenzylphosphine oxide (yield up to 61%). Under similar conditions, phosphorylation of benzy
