Extracurricular laboratory:new discovery of 1,2-Bis(diphenylphosphino)benzene

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An article , which mentions 13991-08-7, molecular formula is C30H24P2.13991-08-7, The compound – 1,2-Bis(diphenylphosphino)benzene played an important role in people’s production and life.

Ferrous carbonyl dithiolates as precursors to FeFe, FeCo, and FeMn carbonyl dithiolates

Reported are complexes of the formula Fe(dithiolate)(CO) 2(diphos) and their use to prepare homo- and heterobimetallic dithiolato derivatives. The starting iron dithiolates were prepared by a one-pot reaction of FeCl2 and CO with chelating diphosphines and dithiolates, where dithiolate = S2(CH2)2 2- (edt2-), S2(CH2)3 2- (pdt2-), S2(CH2) 2(C(CH3)2)2- (Me2pdt 2-) and diphos = cis-C2H2(PPh2) 2 (dppv), C2H4(PPh2)2 (dppe), C6H4(PPh2)2 (dppbz), C 2H4[P(C6H11)2] 2 (dcpe). The incorporation of 57Fe into such building block complexes commenced with the conversion of 57Fe into 57Fe2I4(iPrOH)4, which then was treated with K2pdt, CO, and dppe to give 57Fe(pdt)(CO)2(dppe). NMR and IR analyses show that these complexes exist as mixtures of all-cis and trans-CO isomers, edt2- favoring the former and pdt2- the latter. Treatment of Fe(dithiolate)(CO)2(diphos) with the Fe(0) reagent (benzylideneacetone)Fe(CO)3 gave Fe2(dithiolate)(CO) 4(diphos), thereby defining a route from simple ferrous salts to models for hydrogenase active sites. Extending the building block route to heterobimetallic complexes, treatment of Fe(pdt)(CO)2(dppe) with [(acenaphthene)Mn(CO)3]+ gave [(CO)3Mn(pdt) Fe(CO)2(dppe)]+ ([3d(CO)]+). Reduction of [3d(CO)]+ with BH4- gave the C s-symmetric mu-hydride (CO)3Mn(pdt)(H)Fe(CO)(dppe) (H3d). Complex H3d is reversibly protonated by strong acids, the proposed site of protonation being sulfur. Treatment of Fe(dithiolate)(CO)2(diphos) with CpCoI2(CO) followed by reduction by Cp2Co affords CpCo(dithiolate)Fe(CO)(diphos) (4), which can also be prepared from Fe(dithiolate)(CO)2(diphos) and CpCo(CO)2. Like the electronically related (CO)3Fe(pdt)Fe(CO)(diphos), these complexes undergo protonation to afford the mu-hydrido complexes [CpCo(dithiolate) HFe(CO)(diphos)]+. Low-temperature NMR studies indicate that Co is the kinetic site of protonation.

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Reference£º
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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Mechanism of silver(I)-catalyzed Mukaiyama aldol reaction: Active species in solution in AgPF6-(S)-BINAP versus AgOAc-(S)-BINAP systems

Silver(I)-diphosphine complex is an effective catalyst for Mukaiyama Aldol reaction in polar solvents. AgPF6-(S)-BINAP cationic chiral complex indicated a good activity and could afford fairly high enantioselectivity in the reaction of aromatic aldehydes and silyl enol ethers. On the other hand, AgOAc-(S)-BINAP system afforded the aldol product of the absolute configuration opposite to that by AgPF6-(S)-BINAP and very high catalytic activity was shown. The structure and equilibrium state of Ag(I)-BINAP complexes in solution were examined to understand the reaction mechanism. In AgPF6 system [Ag((S)-BINAP)2]PF6 (1a), [Ag((S)-BINAP)]PF6 (1b), [Ag2((S)-BINAP)](PF6)2 (1c) and AgPF6 are present in solution. The active species of the aldol reaction in DMF is [Ag((S)-BINAP)]PF6 (1b), which exists as a minor species in solution. For this cationic Ag(I) catalyst, cyclic transition state containing substrate and silyl enol ether is assumed. In AgOAc-(S)-BINAP system, active species is also monomeric AgOAc((S)-BINAP) (2b) species which exists as a major component in solution and strong interaction was observed with a silyl enol ether. The reaction by AgOAc-(S)-BINAP catalyst is concluded to proceed as follows: nucleophile forms a complex with AgOAc-(S)-BINAP species and is activated. This complex attacks aldehydes to afford aldol adduct via acyclic transition state.

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Reference£º
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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13991-08-7, 1,2-Bis(diphenylphosphino)benzene is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

An oven dried 200 mL two-necked flask equipped with a magnetic stirring bar and a reflux condenser was charged with a solution of anhydrous lion (II) bromide (1.5 g, 6.95 mmol) and 1,2-bis (diphenylphosphino) benzene (3.41 g, 7.65 mmol) in ethanol (70 mL). The reaction flask was heated to 80 C for 18 hours, at this time pale brown colored precipitate was formed. The reaction mixture was cooled to room temperature. Filtered the brown solid and was washed with 100 mL of hot ethanol. The resulting yellowish brown solid 5a (3.54 g, 77%) was dried under high vacuum for 12 hours.

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Reference£º
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; KISHI, Yoshito; YAHATA, Kenzo; KUMAR, Vemula, Praveen; VADDELA, Sudheer, Babu; (137 pag.)WO2019/9956; (2019); A1;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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13991-08-7, 1,2-Bis(diphenylphosphino)benzene is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a MeCN (20 mL) solution of precursor A (106 mg, 0.229 mmol) was added Me3NO¡¤2H2O(65 mg, 0.58 mmol) under N2, resulting in a color change from red to brown, and stirred atroom temperature for about 20 min. A solution of dppbz (120 mg, 0.269 mmol) in MeCN(20 mL) was added to the above brown solution through a catheter and the resulting solutionwas stirred at room temperature for about 2 h and then reuxed at 60 C for about 12 h. Thereaction was monitored by IR spectroscopy to ensure completion. Upon removing the solventunder reduced pressure, the crude product was puried by chromatography on silica gelusing CH2Cl2/petroleum ether (v/v = 4:5) as eluent. Complex 1 was collected as a green solid(72 mg, 33%). IR (KBr disk, cm-1): nuC?O 2019 (vs), 1953 (vs), 1905 (v). 1H NMR (400 MHz, CDCl3,ppm): 1.68 (t, 2 H, 2JHaHe = 3JHaHa? = 12.6 Hz, 2 SCHaHe), 2.03 (m, 1 H, CH), 2.34 (d, 2 H,2JHeHa = 12.4 Hz, 2 SCHaHe), 6.18 (d, 2 H, Ph), 7.03 (m, 3 H, Ph), 7.21-7.26 (m, 8 H, Ph), 7.35-7.42(m, 10 H, Ph), 7.73-7.76 (m, 6 H, Ph). 31P NMR (161.9 MHz, CDCl3, 85% H3PO4, ppm): 88.2 (s).Anal. Calc. for C43H34Fe2O4P2S2: C, 60.58; H, 4.02. Found: C, 60.31; H, 4.30.

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Reference£º
Article; Guo, Ge; Gao, Hui-Ling; Shen, Feng-Sha; Ge, Shi-Wei; Shang, Jing-Yan; Li, Chang-Gong; Journal of Coordination Chemistry; vol. 70; 15; (2017); p. 2695 – 2707;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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45.6mg mesityl -Cu and 3ml of toluene were added to 48.5mg (0.25mmol) of 7-PyIn and 111.5mg (0.25 mmol) of dppb in a glove box. It forms ayellow solution. It was filtered and coated with a layer of hexane. It formsorange-red crystals. Under UV (356nm), they emit light in a strong orange.Yield: 71%., 13991-08-7

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Reference£º
Patent; MERCK PATENTGMBH; WESEMANN, LARS; KLEIH, MATTHIAS; MAYER, HERMANN, AUGUST; (72 pag.)JP2016/501830; (2016); A;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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13991-08-7, 1,2-Bis(diphenylphosphino)benzene is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of CuCl (19.6mg, 0.2mmol) and dppb (89.3mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and 17 CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. Yield: 80%. Anal. Calc. for C54H40ClCuN2P2: C, 73.83; H, 4.59; N, 3.19. Found: C, 73.62; H, 4.73; N, 3.06%. IR (KBr disc, cm-1): 3652m, 3279w, 3049w, 1962w, 1614m, 1555m, 1514w, 1481m, 1433w, 1410w, 1384w, 1226m, 1095s, 1025w, 865s, 836m, 769s, 745s, 696vs, 663w, 628w, 529s, 484s. 1H NMR (600MHz, CDCl3, 298K) delta 8.39ppm (d, 2H), 8.06ppm (d, 2H), 7.74ppm (d, 2H), 7.69ppm (m, 4H), 7.63ppm (m, 10H), 7.41-7.31ppm (m, 20H); 1P NMR (400MHz, CDCl3, 298K) delta -2.62ppm.

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Reference£º
Article; Yu, Xiao; Fan, Weiwei; Wang, Guo; Lin, Sen; Li, Zhongfeng; Liu, Min; Yang, Yuping; Xin, Xiulan; Jin, Qionghua; Polyhedron; vol. 157; (2019); p. 301 – 309;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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13991-08-7, 1,2-Bis(diphenylphosphino)benzene is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

42.5 mg mesityl -Cu and 3ml of Toluene were added to 46.3(0.23 mmol) of 7-TpIn and 103.7mg (0.23 mmol) of dppb in a glove box. It formsa yellow solution. It was dried in vacuum, dissolved in dichloromethane and coatedwith a layer of hexane. It forms yellow crystals. Under UV (356nm), these emitlight in a strong yellow. Yield: 68%.

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Reference£º
Patent; MERCK PATENTGMBH; WESEMANN, LARS; KLEIH, MATTHIAS; MAYER, HERMANN, AUGUST; (72 pag.)JP2016/501830; (2016); A;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Simple exploration of 13991-08-7

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13991-08-7, 1,2-Bis(diphenylphosphino)benzene is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under argon atmosphere, 1,2-bis(diphenylphosphino)benzene (34.6 mg, 0.0776 mmol) was added to 5 mL of the solution of silver(I) tetrafluoroborate (15.1 mg, 0.0776 mmol) in dichloromethane, and the mixture was stirred at room temperature for 30 minutes. Then, 2,9-dichloro-1,10-phenanthroline (23.2 mg, 0.0931 mmol) was added to the reaction solution, which was heated to reflux with stirring for two hours. The reaction solution was filtrated, and the filtrate was concentrated, subjected to recrystallization by slow diffusion of dichloromethane-ether, and dried to provide 46.0 mg of the yellow solid complex. [Show Image] The NMR data of the obtained complex is provided below. 1H NMR (300 MHz, CDCl3) delta 8.80 (d, J = 8.1 Hz, 2H), 8.24 (s, 2H), 8.15 (d, J = 8.1 Hz, 2H), 7.62-7.51 (m, 4H), 7.39-7.29 (m, 20H); 31P NMR (122 MHz, CDCl3) delta -4.4 (d, J (31P-107Ag, 109Ag) = 325, 373 Hz). The composition of the obtained complex was determined according to the same method as in Example 15. The present complex corresponds to the above composition formula (5).

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Reference£º
Patent; Sumitomo Chemical Company, Limited; EP2360162; (2011); A1;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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The experimental multi-tooth phosphine coordination silver complex double emitting dye synthesis method according to the following steps:1 mmol of multidentate phosphine ligand, 1 mmol of AgI, 5 ml of DCM were mixed and reacted at 40 C. for 10 hours. The mixture was spin-dried and purified by column chromatography with DCM and PE to obtain a multidentate phosphine coordination silver complex.Wherein the ratio of multidentate phosphine ligand to AgI is 1: 1.The volume ratio of DCM to PE in the mixed solvent of DCM and PE is 1:20.

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Reference£º
Patent; Heilongjiang University; Xu Hui; Zhang Jing; Han Chunmiao; (47 pag.)CN106833010; (2017); A;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

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General procedure: Synthesis of the phosphine oxidesThe phosphine oxides were synthesized by oxidation ofthe corresponding phosphines. Calculated amounts of H2O2(30%) were added slowly to the vigorously stirred THF solutionof the respective phosphine. Stirring was maintainedat room temperature for 2 h. After evaporation of THF, theresidue was treated with acetone-ethyl acetate to obtain therespective phosphine oxide product as a precipitate. The precipitatesthus obtained were filtered off and dried in a vacuum.All melting points were above 360 C with decomposition. OPPO: 1H NMR (250 MHz, CDCl3): d = 7:19 (m, 8H,Phen-H), 7.35 (m, 12H, Phen-H), 7.57 (t, 2H, Phen-H), 7.75(m, 2H, Phen-H). – MS (EI): m=z = 478. Yield 82%.

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Reference£º
Article; Pietraszkiewicz, Marek; Mal, Suraj; Pietraszkiewicz, Oksana; Gorski, Krzysztof; Chelwani, Nitin; Zeitschrift fur Naturforschung, B: Chemical Sciences; vol. 69; 2; (2014); p. 239 – 247;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate