- A cyclodiphosphazane based pincer ligand, [2,6-{μ-(tBuN)2P(tBuHN)PO}2C6H3I]: NiII, PdII, PtII and CuI complexes and catalytic studies
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Synthesis and late-transition metal complexes of pincer capable cyclodiphosphazane, 2,6-{μ-(tBuN)2P(tBuHN)PO}2C6H3I (1) are described. The condensation of 2-iodoresorcinol with cis-{ClP(μ-NtBu)2PN(H)tBu} produced a difunctional derivative 1 in good yield. The treatment of Ni(COD)2, Pd2(dba)3·CHCl3 or Pt(PPh3)4 with 1 afforded pincer complexes [2,6-{μ-(tBuN)2P(tBuHN)PO}2C6H3MI] (2 M = Ni; 3 M = Pd and 4 M = Pt). The reaction of complex 3 with copper halides resulted in the formation of heterobimetallic complexes bridged by rhombic {Cu(μ-X)}2 units, [{{Cu(μ-X)}2}{μ-(tBuN)2P(tBuHN)PO}2C6H3PdI] (5 X = I and 6 X = Br). The crystal structures of 1-3, 5 and 6 were established by single X-ray diffraction studies. The palladium complex 3 was tested for catalytic P-arylation of diphenylphosphine oxide (Ph2P(O)H) under microwave irradiation. Moderate to good catalytic activity was observed with aryl bromides. This journal is
- Ananthnag, Guddekoppa S.,Mague, Joel T.,Balakrishna, Maravanji S.
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- Nickel-catalyzed C–P cross-coupling of (het)aryl tosylates with secondary phosphine oxides
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A novel and convenient approach to the synthesis of various tertiary phosphine oxides via nickel-catalyzed cross-coupling of (het)aromatic tosylates with secondary phosphine oxides is developed. The reaction employs cheap nickel as the catalyst, 1-(2-(di-tert-butylphosphanyl)phenyl)-4-methoxypiperidine (L3) as the ligand, and pyridine as the base. This reaction produces the corresponding (het)aromatic phosphorus compounds in good to high yields. Moreover, four new tertiary phosphine oxides are reported in this process.
- He, Xiao-Yun
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p. 747 - 752
(2021/02/26)
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- Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine
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A simple synthetic method of triarylphosphine compounds by KOH-promoted P-Arylation reaction of aryl halides with diphenylphosphine is presented. Notably, this transformation could smoothly proceed with high yields under transition-metal-free and mild reaction conditions. In addition, this protocol is valuable for industrial application due to the convenient operation and readily accessible aromatic halides. A possible explanation of the reaction mechanism was proposed based on the experimental data.
- Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhou, Yang
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- Cu/Picolinamides-Catalyzed Coupling of (Hetero)aryl Halides with Secondary Phosphine Oxides and Phosphite?
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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.
- Fang, Chao,Wei, Bangguo,Ma, Dawei
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supporting information
p. 2957 - 2961
(2021/08/23)
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- Visible-Light-Induced Nickel-Catalyzed P(O)-C(sp2) Coupling Using Thioxanthen-9-one as a Photoredox Catalysis
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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
- Zhu, Da-Liang,Jiang, Shan,Wu, Qi,Wang, Hao,Chai, Lu-Lu,Li, Hai-Yan,Li, Hong-Xi
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supporting information
p. 160 - 165
(2021/01/09)
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- NiCl 2as a Cheap and Efficient Precatalyst for the Coupling of Aryl Fluorosulfonate and Phosphite/Phosphine Oxide
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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.
- Yan, Wenjie,Zhou, Hongbo,Li, Haoyuan,Hu, Huimin,Yu, Ying,Guo, Shengmei,Cai, Hu
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p. 1453 - 1456
(2021/07/20)
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- Palladium-Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)–H Compounds
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A direct decarbonylative phosphorylation of benzoic acids catalyzed by palladium was disclosed. Under the reaction conditions, a wide range of benzoic acids coupled readily with all the three kinds of P(O)–H compounds, i.e. secondary phosphine oxides, H-phosphinates and H-phosphonates, producing the corresponding organophosphorus compounds in good to high yields. This reaction could be conducted at a gram scale and applied in the late-stage phosphorylative modification of carboxylic acids drug molecules. These results well demonstrated the potential synthetic value of this new reaction in organic synthesis.
- Zhang, Ji-Shu,Chen, Tieqiao,Han, Li-Biao
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supporting information
p. 1148 - 1153
(2020/02/27)
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- Aromatic phosphorus oxide compounds and preparation method for aromatic phosphorus oxide medicines of same
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The invention discloses a plurality of aromatic phosphorus oxide compounds and a preparation method of aromatic phosphorus oxide medicines of the same. The preparation method comprises the following steps: weighing 1.2 times equivalent of aromatic carboxy
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Paragraph 0049-0050
(2019/12/25)
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- General Oxidative Aryl C-P Bond Formation through Palladium-Catalyzed Decarbonylative Coupling of Aroylhydrazides with P(O)H Compounds
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Oxidative C-C/P-H cross-coupling is achieved via Pd-catalyzed decarbonylative cross-coupling of aroylhydrazides with P(O)H compounds. The unique cooperative reaction system, especially the Br?nsted acid and bidentate phosphine ligand, allows the selective activation of the inert C-C bond and the suppression of the undesired oxidation and coordination of >P(O)-H compounds, leading to a general oxidative synthesis of aryl phosphorus compounds from easily available substrates.
- Dong, Jianyu,Liu, Long,Ji, Xuyu,Shang, Qian,Liu, Lixin,Su, Lebin,Chen, Bing,Kan, Ruifeng,Zhou, Yongbo,Yin, Shuang-Feng,Han, Li-Biao
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supporting information
p. 3198 - 3203
(2019/05/10)
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- Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds
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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.
- Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
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supporting information
p. 1150 - 1153
(2018/02/23)
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- Preparation of organophosphorus compounds from P-H compounds using o-(trimethylsilyl)aryl triflates as aryne precursors
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An efficient method was developed for the synthesis of a variety of arylphosphorus compounds from P-H compounds using o-(trimethylsilyl)aryl triflates as aryne precursors. The reaction provides a practical preparation of various arylphosphorus compounds via aryne intermediates utilizing diarylphosphine oxides and dialkyl phosphites as the nucleophiles.
- Yang, Guoqiang,Shen, Chaoren,Quan, Mao,Zhang, Wanbin
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supporting information
p. 333 - 337
(2015/12/30)
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- Nickel-catalyzed C-P cross-coupling of arylboronic acids with P(O)H compounds
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A novel and efficient Ni-catalyzed coupling of a wide range of arylboronic acids with H-phosphites, H-phosphinate esters, and H-phosphine oxides has been developed, providing a general and powerful tool for the synthesis of various aryl-phosphorus compounds, especially for valuable triarylphosphine oxides, in good to excellent yield. This protocol is the first Ni-catalyzed C-P bond-forming reaction between arylboronic acids and P(O)H compounds.
- Hu, Gaobo,Chen, Weizhu,Fu, Tingting,Peng, Zhimin,Qiao, Hongwei,Gao, Yuxing,Zhao, Yufen
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supporting information
p. 5362 - 5365
(2013/11/06)
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- Nickel-catalyzed C-P coupling of aryl mesylates and tosylates with H(O)PR1R2
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A method was developed for the nickel-catalyzed phosphonylation of aryl mesylates and tosylates with H(O)PR1R2. To the best of our knowledge, this is the first example of nickel-catalyzed C-P coupling of aryl mesylates and tosylates. Most of the substrates gave moderate to good yields under our catalytic system.
- Shen, Chaoren,Yang, Guoqiang,Zhang, Wanbin
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supporting information; experimental part
p. 3500 - 3505
(2012/05/20)
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- Manganese(III)-mediated direct phosphonylation of arenes
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Manganese (III)-promoted direct phosphonylation of mono- and disubstituted arenes with dialkylphosphite afforded regioselective dialkylphosphonates in good yields. The reactions can apply to arenes bearing electron-donating groups and electron-withdrawing
- Xu, Wei,Zou, Jian-Ping,Zhang, Wei
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supporting information; experimental part
p. 2639 - 2643
(2010/06/16)
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- New Chiral Diphosphine Ligands Designed to Have a Narrow Dihedral Angle in the Biaryl Backbone
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A series of novel optically active diphosphine ligands, (4,4′-bi-1,3-benzodioxole)-5,5′-diylbis(diarylphosphine)s (6), which are called SEGPHOS, has been designed and synthesized with dihedral angles in the Ru complexes being less than that in the corresponding BINAP-Ru complex. The stereorecognition abilities of SEGPHOS-Ru complex catalysts in the asymmetric catalytic hydrogenation of a wide variety of carbonyl compounds are superior to those observed with BINAP-Ru complex catalysts.
- Saito, Takao,Yokozawa, Tohru,Ishizaki, Takero,Moroi, Takashi,Sayo, Noboru,Miura, Takashi,Kumobayashi, Hidenori
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p. 264 - 267
(2007/10/03)
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- Chiral diphosphine compound intermediate for preparing the same transition metal complex having the same diphosphine compound as ligand and asymmetric hydrogenation catalyst
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A novel diphosphine compound of the formula (I): STR1 where R1 and R2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.
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