2373-43-5Relevant academic research and scientific papers
Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions
Farrokhi, Alireza,Rouzifar, Majid,Sansano, José Miguel,Sobhani, Sara
, p. 19963 - 19976 (2021/11/12)
A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.
Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride
Zhang, Yiyuan,Chen, Wanting,Tan, Tingting,Gu, Yuang,Zhang, Shuning,Li, Jie,Wang, Yan,Hou, Wei,Yang, Guang,Ma, Peixiang,Xu, Hongtao
, p. 4588 - 4591 (2021/05/17)
We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).
A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water
Sobhani, Sara,Hosseini Moghadam, Hadis,Skibsted, J?rgen,Sansano, José Miguel
, p. 1353 - 1365 (2020/03/11)
A hydrophilic heterogeneous cobalt catalyst of chitosan, denoted as mTEG-CS-Co-Schiff-base, has been successfully prepared. This newly synthesized catalyst was characterized by different methods such as XRD, FE-SEM, TEM, TGA, FT-IR, 13C{1H} CP/MAS NMR, XPS and ICP analyses. The catalyst displayed excellent activity for the palladium and fluoride-free Hiyama, Suzuki, Heck and Hirao reactions of various aryl iodides, bromides and chlorides (i.e., the most challenging aryl halides which are cheaper and more widely available than aryl iodides and bromides) in water. The presence of triethylene glycol tags with hydrophilic character on the Co-complex supported on chitosan provides dispersion of the catalyst particles in water, which leads to higher catalytic performance and also facile catalyst recovery by successive extraction. It was reused for at least six successive runs without any discernible decrease in its catalytic activity or any remarkable changes in catalyst structure. The use of water as a green solvent, without requiring any additive or organic solvent, as well as use of a low cost and abundant cobalt catalyst instead of expensive Pd catalysts along with the catalyst recovery and scalability, make this method favorable from environmental and economic points of view for the C-C and C(sp2)-P coupling reactions. Notably, this is the first report on the application of a cobalt catalyst in Hiyama reactions.
Arylphosphate compound and preparation method thereof
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Paragraph 0011; 0016, (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.
Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides
Bai, Ya,Liu, Nian,Wang, Shutao,Wang, Siyu,Ning, Shulin,Shi, Lingling,Cui, Lili,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 6835 - 6838 (2019/09/30)
A nickel-catalyzed electrochemical cross-coupling reaction of aryl bromides with dialkyl phosphites, ethyl phenylphosphinate, and diphenylphosphine oxide has been developed. This reaction utilizes a simple undivided cell with inexpensive carbon electrodes to synthesize aryl phosphonates, aryl phosphinates, and arylphosphine oxides at room temperature. This protocol provides a mild and efficient route for the construction of C-P bond in moderate to high yields with broad substrate scope.
Decarbonylative Phosphorylation of Carboxylic Acids via Redox-Neutral Palladium Catalysis
Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal
supporting information, p. 9256 - 9261 (2019/11/19)
We describe the direct synthesis of organophosphorus compounds from ubiquitous aryl and vinyl carboxylic acids via decarbonylative palladium catalysis. The catalytic system shows excellent scope and tolerates a wide range of functional groups (>50 examples). The utility of this powerful methodology is highlighted in the late-stage derivatization directly exploiting the presence of the prevalent carboxylic acid functional group. DFT studies provided insight into the origin of high bond activation selectivity and P(O)-H isomerization pathway.
C-P bond construction catalyzed by NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII
Ghasemzadeh, Maryam Sadat,Akhlaghinia, Batool
, p. 5341 - 5356 (2019/04/05)
NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII) was prepared as a stable, h
Catalyst-free phosphorylation of aryl halides with trialkyl phosphites through electrochemical reduction
Wang, Shuai,Yang, Cheng,Sun, Shuo,Wang, Jianbo
supporting information, p. 14035 - 14038 (2019/11/25)
A catalyst-free electrochemical cross-coupling reaction of aryl halides with trialkyl phosphite has been developed. This reaction proceeds in an undivided cell with a low-cost Ni anode and a graphite cathode under mild and neutral conditions. A wide range of functional groups are well-tolerated and the phosphorylated product can be obtained on the gram scale, showing that this transformation has the potential to be a valuable method for the construction of aromatic carbon-phosphorus bonds.
Synthesis, characterization and properties of titanium phosphonate clusters
Hayami, Ryohei,Sagawa, Takuya,Tsukada, Satoru,Yamamoto, Kazuki,Gunji, Takahiro
supporting information, p. 1 - 8 (2018/04/02)
Titanium phosphonate clusters were synthesized by the reactions of titanium tetraisopropoxide (Ti(OiPr)4) with arylphosphonic acids (ArPO3H2, Ar = Ph, 1-Nap, 4-MeOPh, 4-FPh, 4-ClPh, 4-BrPh, and 4-BrBn) and H2O in tetrahydrofuran (THF) at room temperature. [Ti4(μ3-O)(OiPr)5(μ-OiPr)3(O3PAr)3]·solv (Ar = Ph (1), 1-Nap (2), 4-MeOPh (3), 4-FPh (4), 4-ClPh (5); solv = thf for 1 and 2 or 2-propanol for 3–5) were isolated as new Ti4P3-type clusters, while Ti7(μ3-O)2(OiPr)6(μ-OiPr)6(O3PBnBr)6 (6) was isolated as a Ti7P6-type cluster. A co-crystal of Ti4P3- (7a) and Ti7P6-type (7b) clusters were obtained when 4-BrPhPO3H2 was used, and [Ti(OiPr)(acac)(O3PPh)]4 (8), a new cage cluster, was obtained when Ti(acac)2(OiPr)2 (Hacac = acetylacetone) was reacted with PhPO3H2.
Cu2O/TiO2 nanoparticles as visible light photocatalysts concerning C(sp2)-P bond formation
Hosseini-Sarvari, Mona,Jafari, Fattaneh,Mohajeri, Afshan,Hassani, Nasim
, p. 4044 - 4051 (2018/08/24)
A novel and efficient method has been developed for the construction of an aromatic-phosphorus (Ar-P) bond under visible light irradiation using Cu2O/TiO2 nanoparticles as inexpensive and available photocatalysts. This protocol is a simple system without the use of any base, ligand, oxidant, or special conditions. This is the first report for the synthesis of arylphosphonates from arylhydrazines in visible light irradiation.
