5032-54-2Relevant academic research and scientific papers
Palladium anchored on a covalent organic framework as a heterogeneous catalyst for phosphorylation of aryl bromides
Chen, Yu-Xuan,Zhang, Shuo,Xue, Yu-Jie,Mo, Li-Ping,Zhang, Zhan-Hui
, (2021/11/05)
A simple azine-linked covalent organic framework (COF) with high thermal and chemical stabilities has been prepared by using deep eutectic solvent (DES) as green media. The as-synthesized COF was employed as heterogeneous ligand for immobilization of PdII. The obtained Pd-supported COF nanoparticles catalyst (defined as Pd/TFPT-Azine-COF) was found to be an efficient heterogeneous catalyst for the Hirao reaction of aryl halides and dialkyl phosphites or diphenylphosphine oxide with excellent recyclability, reusability, and retention of crystallinity.
Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide
McErlain, Holly,Riley, Leanne M.,Sutherland, Andrew
, p. 17036 - 17049 (2021/11/18)
An iodide-accelerated, palladium-catalyzed C-P bond-forming reaction of aryl nonaflates is described. The protocol was optimized for the synthesis of aryl phosphine oxides and was found to be tolerant of a wide range of aryl nonaflates. The general nature of this transformation was established with coupling to other P(O)H compounds for the synthesis of aryl phosphonates and an aryl phosphinate. The straightforward synthesis of stable, isolable aryl nonaflates, in combination with the rapid C-P bond-forming reaction allows facile preparation of aryl phosphorus target compounds from readily available phenol starting materials. The synthetic utility of this general strategy was demonstrated with the efficient preparation of an organic light-emitting diode (OLED) material and a phosphonophenylalanine mimic.
NiCl 2as a Cheap and Efficient Precatalyst for the Coupling of Aryl Fluorosulfonate and Phosphite/Phosphine Oxide
Yan, Wenjie,Zhou, Hongbo,Li, Haoyuan,Hu, Huimin,Yu, Ying,Guo, Shengmei,Cai, Hu
, p. 1453 - 1456 (2021/07/20)
Herein, NiCl 2is employed as a cheap precatalyst in the formation of C(sp 2)-P bond via cross-coupling reaction of phenol derivatives and phosphine oxides/phosphites. This catalytic system allows a variety of phenols with diverse functional groups to transform into phosphates with good yields. No additional additive is used in this reaction.
Method for synthesizing trisubstituted arylphosphine oxide species by using diphenyl(tert-butyl)phosphine as substrate
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Paragraph 0019-0020; 0021-0023, (2021/07/28)
The invention relates to a method for synthesizing a trisubstituted arylphosphine oxide species by taking diphenyl(tert-butyl)phosphine as a substrate, belonging to the technical field of organic phosphine synthesis. The method comprises the following steps: with a transition metal palladium salt as a catalyst and a hydrazine compound and diphenyl(tert-butyl)phosphine as reaction substrates, adding the reaction substrates and an alkali compound into a reaction solvent, carrying out stirring and heating, conducting reacting for a certain period of time to obtain a reaction solution, and separating and purifying the reaction solution to obtain a trisubstituted arylphosphine oxide compound, wherein the hydrazine compound is any one selected from aromatic hydrazine and aromatic heterocyclic hydrazine; and the transition metal palladium salt catalyst is selected from any one of Pd(OAc)2, Pd(dba)2 and PdCl2. Compared with a traditional synthesis method, the method has the advantages that the use of diarylphosphine oxide hydrogen is avoided, raw materials are easy to obtain, reaction conditions are mild, yield is high, and reaction selectivity is good. In general, the method is friendly to environment and simple in synthesis process, and has certain industrial application prospects.
Preparation method of aromatic phosphine oxide compound
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Paragraph 0052-0054, (2021/10/20)
The invention relates to the field of organic synthesis, in particular to a preparation method of an aromatic phosphine oxide compound. The preparation method comprises the following steps: adding a P(O)-H compound, a fluoroaromatic compound and an alkali reagent into an organic solvent, conducting mixing, performing stirring for reaction, and carrying out cooling to obtain a mixed solution; and carrying out washing and extracting to obtain an organic phase, drying and distilling the organic phase, and performing column chromatography to obtain the aromatic phosphine oxide compound. The method is simple in reaction operation, only a proper amount of alkali needs to be added, special reaction conditions such as ligands, catalysts and additives are not needed, the reaction is simple and efficient, and good industrial application prospects are achieved.
Visible-Light-Induced Nickel-Catalyzed P(O)-C(sp2) Coupling Using Thioxanthen-9-one as a Photoredox Catalysis
Zhu, Da-Liang,Jiang, Shan,Wu, Qi,Wang, Hao,Chai, Lu-Lu,Li, Hai-Yan,Li, Hong-Xi
supporting information, p. 160 - 165 (2021/01/09)
An efficient method has been developed for photocatalytic P(O)-C(sp2) coupling of (hetero)aryl halides with H-phosphine oxides or H-phosphites under the irradiation of visible light or sunlight. The thioxanthen-9-one/nickel dual catalysis mediates this ph
Cu/Picolinamides-Catalyzed Coupling of (Hetero)aryl Halides with Secondary Phosphine Oxides and Phosphite?
Fang, Chao,Wei, Bangguo,Ma, Dawei
supporting information, p. 2957 - 2961 (2021/08/23)
Some 4-hydroxy-picolinic acid derived amides were revealed as more efficient ligands for Cu-catalyzed coupling of (hetero)aryl halides with secondary phosphine oxides and phosphites. Only 3—5 mol% CuI and ligands were required to ensure coupling with a number of (hetero)aryl bromides and iodides to complete at 120 oC in 10—20 h.
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.
Practical C–P bond formation via heterogeneous photoredox and nickel synergetic catalysis
Koranteng, Ernest,Liu, Yi-Yin,Liu, Si-Yue,Wu, Qiang-Xian,Lu, Liang-Qiu,Xiao, Wen-Jing
, p. 1841 - 1846 (2019/11/11)
An efficient C–P bond formation reaction was developed by virtue of the synergetic catalysis strategy by merging heterogeneous photocatalysis and nickel catalysis. This platform utilizing cadmium sulfide semiconductors as heterogeneous photocatalysts and
Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds
Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
supporting information, p. 1150 - 1153 (2018/02/23)
Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.
