Tag: M.W:200-300

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Influence of water on the deprotonation and the ionic mechanisms of a Heck alkynylation and its resultant E-factors

The influence of water on deprotonation and ionic mechanisms of a Heck alkynylation and its resultant E-factors were investigated. Estimation of the Hatta modulus, MH < 0.02, in cationic deprotonation, anionic deprotonation, and the ionic mechanism each separately confirmed an infinitely slow rate of reaction with respect to the diffusive flux within the thin film of the immiscible aqueous-organic interface. As a consequence, intrinsic kinetic expressions for far-equilibrium conditions were derived from first principles for each mechanism. Analyses of Gibbs free energies revealed that water potentially switched the rate-determining steps of cationic and anionic deprotonation to any of oxidative addition of organohalide to form Pd-complex (DeltaG++ = 97.6 kJ mol-1), coordination of the alkyne with the oxidative addition adduct (DeltaG++ = 97.6 kJ mol-1), or ligand substitution to form the cationic Pd-complex (DeltaG++ = 94.9 kJ mol-1). Hydrogen-bonding in the transfer mechanism might account for the switch. Water, in general, was found to influence which step governs each catalytic cycle and the magnitude of its Gibbs free energy. Transformation of the synthesis from batch to continuous-flow was also studied by analyses of E-factors within the thin film. The amount of waste generated, as indicted by estimations of E-factors, was less in continuous-flow operation than in batch when the fastest step of deprotonation (ligand substitution) was infinitely fast with respect to the diffusive flux. The concentration of hydrophilic phosphine ligand was observed to influence mass transport limitations and the E-factor. Increasing ligand concentrations beyond (10.5), (13.3), and (23.2) ¡Á 10-3 mol L-1 for reaction temperatures of 353, 343, and 323 K increased the E-factor above its minimum value of 4.7, and it also induced mass-Transfer-limitations. The switch from intrinsic to mass-Transport-limited kinetics by finite changes in the ligand concentration explains ambiguity when performing aqueous-phase catalyzed Heck alkynylations and possibly multiphase Pd-catalyzed C-C cross-couplings in general. The potential exists to inadvertently mask the reactivity of useful ligands during discovery and to force mass transport limitations during manufacture. Understanding why the E-factor can be minimized is vital to the sustainable discovery and manufacture of fine chemicals, materials, natural products, and pharmaceuticals. If you are hungry for even more, make sure to check my other article about 224311-51-7. Related Products of 224311-51-7

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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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AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY

Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.

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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 catalytic hydroaminomethylation of long chain alkenes with dimethylamine in aqueous-organic two-phase system

Hydroaminomethylation of long chain alkenes with dimethylamine was investigated. The reaction was catalyzed by a water-soluble rhodium-phosphine complex, RhCl(CO)(TPPTS)2 [TPPTS: P(m-C6H 4SO3Na)3], in an aqueous-organic two-phase system in the presence of the cationic surfactant cetyltrimethylammonium bromide (CTAB). The reaction was friendly for the environment since it was free from any organic solvent. The addition of the cationic surfactant CTAB accelerated the reaction, apparently due to the micelle effect. The effects of various reaction parameters (such as reaction temperature, pressure, molar ratio of phosphine ligand to rhodium, catalyst concentration, molar ratio of dimethylamine to alkene and chain length of alkenes) on hydroaminomethylation were studied. High reactivity and selectivity for tertiary amine were achieved under relatively mild conditions (130C, 3MPa).

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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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Preparation and catalytic studies of palladium nanoparticles stabilized by dendritic phosphine ligand-functionalized silica

Silica is a prominently utilized heterogeneous metal catalyst support. Functionalization of the silica with poly(ether imine) based dendritic phosphine ligand was conducted, in order to assess the efficacy of the dendritic phosphine in reactions facilitated by a silica supported metal catalyst. The phosphinated poly(ether imine) (PETIM) dendritic ligand was bound covalently to the functionalized silica. For this purpose, the phosphinated dendritic ligand containing an amine at the focal point was synthesized initially. Complexation of the dendritic phosphine functionalized silica with Pd(COD)Cl2 yielded Pd(II) complex, which was reduced subsequently to Pd(0), by conditioning with EtOH. The Pd metal nanoparticle thus formed was characterized by physical methods, and the spherical nanoparticles were found to have >85% size distribution between 2 nm and 4 nm. The metal nanoparticle was tested as a hydrogenation catalyst of olefins. The catalyst could be recovered and recycled more than 10 times, without a loss in the catalytic efficiency.

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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

The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.50777-76-9, Name is 2-(Diphenylphosphino)benzaldehyde, molecular formula is C19H15OP. In a Article£¬once mentioned of 50777-76-9, Recommanded Product: 2-(Diphenylphosphino)benzaldehyde

Formation of 2-Azaallyl Cobalt(I) Complexes by Csp3-H Bond Activation

Three novel unsymmetrical eta3-2-azaallyl cobalt(I) complexes, [(2-PPh2)C6H4]CH?N[CHC6H4(4-R)]Co(PMe3)2 (4-6) (R = H (4); Cl (5); and OMe (6)), were synthesized by the reactions of Schiff base ligands [(2-PPh2)C6H4]CH?N[CH2C6H4(4-R)] (1-3) (R = H (1); Cl (2); and OMe (3)) with CoMe(PMe3)4 via sp3 C-H bond activation under mild reaction conditions. Complex {[(2-PPh2)C6H4]CH?NCH3[CHC6H4(4-R)]Co(PMe3)2}I (7) as an 18e cobalt(III) salt was obtained through the reaction of 4 with iodomethane. The substitution reaction of complex 4 with carbon monoxide afforded the dicarbonyl cobalt(I) complex [(2-PPh2)C6H4]CH[N?CHC6H4(4-R)]Co(CO)2(PMe3) (8). The molecular structures of complexes 4-8 were determined by single crystal X-ray diffraction.

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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 chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2016

This is a review of papers published in the year 2016 that focus on the synthesis, reactivity, or properties of compounds containing a carbon-transition metal double or triple bond. Highlights for the year 2016 include: (1) significant advances in the design of new precursors to carbene complex intermediates (e.g. alkynes, triazoles, and tosylhydrazones) that serve as safer alternatives to potentially hazardous diazo compounds, (2) continued vast employment of olefin metathesis for the synthesis of complex small molecules and polymers, including many examples of Z-selective reactions, (3) design of novel transformations employing metallacumulene intermediates, (4) preparation of novel aromatic ring systems incorporating transition elements, (5) use of gold and platinum carbene-mediated transformations of alkynes in complex synthetic organic transformations, and (6) design of novel reaction pathways for capture of transition metal carbenoid intermediates.

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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

Synthetic Route of 13360-92-4, Chemistry can be defined as the study of matter and the changes it undergoes. You¡¯ll sometimes hear it called the central science because it is the connection between physics and all the other sciences, starting with biology.13360-92-4, Name is Phenoxydiphenylphosphine, molecular formula is C18H15OP. In a patent, introducing its new discovery.

Tuning the cytotoxicity of ruthenium(ii) para-cymene complexes by mono-substitution at a triphenylphosphine/phenoxydiphenylphosphine ligand

The new complexes [RuCl2(eta6-p-cymene)(kappaP-Ph2PR)] [R = 4-C6H4OSiMe2tBu, 1; R = 4-C6H4Br, 2; R = OC(O)CHCl2, 3; R = OPh, 4; R = O(2-C6H4SiMe2tBu), 5] and [Ru(C2O4)(eta6-p-cymene){kappaP-Ph2PO(2-C6H4(SiMe2tBu))}], 6, were obtained in 83-98% yield from Ru(ii) arene precursors by three different synthetic strategies. The unprecedented phosphine Ph2P(O(2-C6H4SiMe2tBu)) was synthesized in 86% yield from 2-C6H4Br(OSiMe2tBu) and Ph2PCl, via intramolecular oxygen to carbon 1,3 migration of the silyl group (retro-Brook rearrangement). All the complexes were fully characterized by analytical and spectroscopic methods, and by single crystal X-ray diffraction in the cases of 3, 4, 5 and 6. Complexes 1-6 and the model compounds [RuCl2(eta6-p-cymene)(kappaP-PPh3)] (Ru-PPh3) and [Ru(C2O4)(eta6-p-cymene)(kappaP-PPh3)] (Ru-PPh3-O) underwent slow degradation in chloroform solutions upon air contact; the mixed valence complex [(eta6-p-cymene)Ru(mu-Cl)3RuCl2(kappaP-PPh3)], 7, was isolated from a solution of Ru-PPh3 in CHCl3, and X-ray identified. The antiproliferative activity of 1-6 and Ru-PPh3, Ru-PPh3-O and [RuCl2(eta6-p-cymene)(kappaP-PTA)] (RAPTA-C) was assessed towards the triple-negative breast cancer cell line MDA-MB-231, the ovarian carcinoma cell line A2780 and human skin fibroblasts (HSF). Complexes 1, 2, 5 and 6 displayed IC50 values significantly lower than that of cisplatin, with 2 providing a more potent cytotoxic effect on MDA-MB-231 and A2780 cancer cells compared to the noncancerous cell line (HSF). The stability of all complexes in DMSO/water solution was elucidated by NMR and conductivity measurements, and in particular 35Cl NMR spectroscopy was helpful to check the possible chloride dissociation. The stability studies suggest that the cytotoxic activity in vitro of the compounds is mainly ascribable to Ru(ii) species still bound to the phosphorus ligand.

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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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A review of the problem of distinguishing true homogeneous catalysis from soluble or other metal-particle heterogeneous catalysis under reducing conditions

This review considers cases in which a discrete transition-metal complex is used as a precatalyst for reductive catalysis; it focuses on the problem of determining if the true catalyst is a metal-complex homogeneous catalyst or if it is a soluble or other metal-particle heterogeneous catalyst. The various experiments that have been used to distinguish homogeneous and heterogeneous catalysis are outlined and critiqued. A more general method for making this distinction is then discussed. Next, the circumstances that make heterogeneous catalysis probable, and the telltale signs that a heterogeneous catalyst has formed, are outlined. Finally, catalytic systems requiring further study to determine if they are homogeneous or heterogeneous are listed. The major findings of this review are: (i) the in situ reduction of transition-metal complexes to form soluble-metal-particle heterogeneous catalysts is common; (ii) the formation of such a catalyst is easy to miss because colloidal solutions often appear homogeneous to the naked eye; (iii) a variety of experiments have been used to distinguish homogeneous catalysis from heterogeneous catalysis, but there is no single definitive experiment for making this distinction; (iv) experiments that provide kinetic information are key to the correct identification of the true catalyst; and (v) a more general approach for distinguishing homogeneous catalysis from heterogeneous catalysis has been developed. Additionally, (vi) the conditions under which a heterogeneous catalyst is likely to form include: (a) when easily reduced transition-metal complexes are used as precatalysts; (b) when forcing reaction conditions are employed; (c) when nanocluster stabilizers are present; and (d) when monocyclic arene hydrogenation is observed. Finally, (vii) the telltale signs of heterogeneous catalysis include the formation of dark reaction solutions, metallic precipitates, and the observation of induction periods and sigmoidal kinetics.

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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

7650-91-1, Name is Benzyldiphenylphosphine, molecular formula is C19H17P, belongs to chiral-phosphine-ligands compound, is a common compound. In a patnet, once mentioned the new application about 7650-91-1, name: Benzyldiphenylphosphine

Synthesis and characterization of diiron ethanedithiolate complexes with monosubstituted phosphine ligands

Reactions of (mu-edt)Fe2(CO)6 (edt = SCH2CH2S) (1) with the monophosphine ligands Ph2PCH2Ph, Ph2PC6H11, Ph2PCH2CH2CH3, or P(2-C4H3O)3 in the presence of Me3NO?2H2O afforded (mu-edt)Fe2(CO)5L [L = Ph2PCH2Ph, 2; Ph2PC6H11, 3; Ph2PCH2CH2CH3, 4; P(2-C4H3O)3, 5] in 70?88% yields. Complexes 2?5 were characterized by spectroscopy and single crystal X-ray diffraction analysis. The phosphorus of 2?5 is in an apical position of the distorted octahedral geometry of iron.

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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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Selectivity control in the palladium-catalyzed cross-coupling of alkyl nucleophiles

Site-selectivity remains a major challenge in metal-catalyzed C-H bond functionalization. Most existing strategies rely on the introduction of a directing group or on the intrinsic reactivity of the substrate. In this account article, we describe the development of an alternative strategy based on the migration of an organopalladium species along an alkyl chain, wherein the phosphine ligand controls the cross-coupling site. This concept was first implemented with lithium enolates, and then extended to alpha-zincated alkylamines obtained by directed lithiation and transmetalation. Both the direct and the migrative cross-couplings, which are controlled by simply switching the ligand, furnish synthetically useful organic intermediates.

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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