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Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

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Bis(2-oxo-7-azaindolin-3-ylidene)benzodifuran-dione-based donor-acceptor polymers for high-performance n-type field-effect transistors

Two donor-acceptor (D-A) conjugated polymers, PBABDF-DT and PBABDF-TVT, were synthesized using a strongly electron-deficient unit, (3E,7E)-3,7-bis(6-bromo-1-(4-decyltetradecyl)-2-oxo-7-azaindolin-3-ylidene)benzo[1,2-b:4,5-b?]difuran-2,6(3H,7H)-dione (BABDF) as the acceptor, and dithiophene and (E)-2-(2-(thiophen-2-yl)vinyl)thiophene as the donor units. Both polymers exhibited low LUMO energy levels (?-4.0 eV) for marching with electron transport and displayed excellent n-type charge transport characteristics. The organic field-effect transistors exhibited the highest electron mobilities of 1.86 cm2 V-1 s-1 and 1.56 cm2 V-1 s-1 with high Ion/Ioff ratios of 1.6 ¡Á 106 and 1.0 ¡Á 106 for PBABDF-DT and PBABDF-TVT, respectively. Both polymers had highly uniform polymer nanofibers, orderly lamellar crystalline structures, and close pi-pi stacking distances which all contributed to the high charge carrier mobility.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Extracurricular laboratory:new discovery of [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

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Synthesis of 2H-chromenes through the reduction of chromones with 9-BBN

Chromones were regioselectively reduced to 2H-1-benzopyrans through the 1,2-addition of 9-borabicyclo-[3.3.1]nonane. Although transition-metal complexes did not have a catalytic effect on the reaction, only by using palladium(II) chloride, could both 2H-1-benzopyran and dihydro-1-benzopyran be obtained to a similar extent. Also, the reduction of chromone using other organoboranes led not to 2H-1-benzopyran, but rather to chromanone through the reduction of only an olefin moiety.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Simple exploration of Pd2(DBA)3

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Polar Side Chain Effects on the Thermoelectric Properties of Benzo[1,2-b:4,5-b?]Dithiophene-Based Conjugated Polymers

The molecular structure of polymers has a great influence on their thermoelectric properties; however, the relationship between the molecular structure of a polymer and its thermoelectric properties remains unclear. In this work, two benzo[1,2-b:4,5-b?]dithiophene (BDT)-based conjugated polymers are designed and synthesized, which contain alkyl side chains or polar side chains. The effects of the polymer side chain on the physicochemical properties are systematically investigated, especially the thermoelectric performance of the polymers after doping with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane. It is found that the BDT-based conjugated polymer with polar side chains exhibits good miscibility with the dopants, leading to higher thermoelectric properties than those of the polymer with alkyl side chains. This work can serve as a reference for the future design of high-performance organic thermoelectric polymers.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Brief introduction of Tris(dibenzylideneacetone)dipalladium-chloroform

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Transmetalation reactions. The role of the stabilizing olefin in determining the overall reaction rate

A systematic study concerning the transmetalation reaction between the palladium butadienyl complexes [PdCl((ZC{double bond, long}CZ)2Me)(L-L?)] (Z = COOMe; L-L? = MeN-SPh (1A), N-SPh (1B), DPPQ-Me (1C), BiPy (1D), DPPE (1E)) and tributyl-phenylethynyl-stannane in the presence of some stabilizing olefins (ma, fn, nq, dmfu, and tmetc) was undertaken. The dependence of the reaction rate on the nature of the ancillary ligand was discussed in terms of the donor capability and steric characteristics of the ligand. It has been noticed that, other things being equal, the joined distorted MeN-SPh ligand imparts the highest reactivity to its derivative (complex 1A). The most surprising issue was however represented by the olefin which seems to affect heavily the reactivity of the starting substrate thereby increasing the overall reaction rate. The most active olefins were ma and fn. In the case of the reaction between the complex 1A and tributyl-phenylethynyl-stannane in the presence of fn an exhaustive kinetic study was carried out and a mechanistic hypothesis was advanced.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

A new application about Pd2(DBA)3

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Nucleophile Coordination Enabled Regioselectivity in Palladium-Catalyzed Asymmetric Allylic C?H Alkylation

Branched selectivity in asymmetric allylic C?H alkylation is enabled by using 2-acylimidazoles as nucleophiles in the presence of a chiral phosphoramidite-palladium catalyst. A wide range of terminal alkenes, including 1,4-dienes and allylarenes, are nicely tolerated and provide chiral 2-acylimidazoles in moderate to high yields and with high levels of regio-, and enantio-, and E/Z-selectivities. Mechanistic studies using density-functional theory calculations suggest a nucleophile-coordination-enabled inner-sphere attack mode for the enantioselective carbon?carbon bond-forming event.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

The Absolute Best Science Experiment for 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex

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3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres

A Pd-catalyzed Miyaura borylation of 3-bromo-2,1-borazaronaphthalenes is reported. This method allows the formation of umpolung reagents for subsequent Pd-mediated cross-coupling. Coupling of this nucleophilic partner with a variety of commercially available aryl- and heteroaryl halides allows facile and rapid diversification of these cores.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Extracurricular laboratory:new discovery of 52409-22-0

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Rational Design of High-Performance Wide-Bandgap (?2 eV) Polymer Semiconductors as Electron Donors in Organic Photovoltaics Exhibiting High Open Circuit Voltages (?1 V)

Systematic optimization of the chemical structure of wide-bandgap (?2.0 eV) ?donor?acceptor? copolymers consisting of indacenodithiophene or indacenodithieno[3,2-b]thiophene as the electron-rich unit and thieno[3,4-c]pyrrole-4,6-dione as the electron-deficient moiety in terms of alkyl side chain engineering and distance of the electron-rich and electron-deficient monomers within the repeat unit of the polymer chain results in high-performance electron donor materials for organic photovoltaics. Specifically, preliminary results demonstrate extremely high open circuit voltages (V ocs) of ?1.0 V, reasonable short circuit current density (J sc) of around 11 mA cm?2, and moderate fill factors resulting in efficiencies close to 6%. All the devices are fabricated in an inverted architecture with the photoactive layer processed by doctor blade equipment, showing the compatibility with roll-to-roll large-scale manufacturing processes. From the correlation of the chemical structure?optoelectronic properties?photovoltaic performance, a rational guide toward further optimization of the chemical structure in this family of copolymers, has been achieved. (Figure presented.).

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Top Picks: new discover of 52409-22-0

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Related Products of 52409-22-0, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 52409-22-0, molcular formula is C51H42O3Pd2, introducing its new discovery.

Palladium-catalysed cross-coupling as a key step in the synthesis of pyridyl-benzamides, -benzylamines and -sulfonamides

Novel N-, O- and S-substituted pyridyl-benzamides, -benzylamines and -sulfonamides were prepared by means of palladium-catalysed cross-coupling reactions. The synthetic approach, using Pd2(dba)3as palladium source and rac-BINAP as supporting ligand, proved to be successful for C[sbnd]N, C[sbnd]O and C[sbnd]S cross-coupling reactions. One of the substrates underwent an unexpected nucleophilic aromatic substitution of fluorine, rather than the expected C[sbnd]N cross-coupling reaction.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method

Can You Really Do Chemisty Experiments About [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)

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Application of 72287-26-4, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 72287-26-4, molcular formula is C34H28Cl2FeP2Pd, introducing its new discovery.

Synthesis of bench-stable solid triorganoindium reagents and reactivity in palladium-catalyzed cross-coupling reactions

Bench-stable solid triorganoindium compounds have been prepared by coordination with 4-(dimethylamino)pyridine (DMAP). The solid R3In(DMAP) complexes are obtained from the corresponding solution of R3In in quantitative yield and can be stored for up to several weeks. These reagents show excellent reactivity in palladium-catalyzed cross-coupling reactions with organic electrophiles.

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Reference£º
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method