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An expedient regioselective synthesis of a GABA alpha2/3 agonist 1 is described. The key step is an efficient regioselective palladium-catalyzed coupling of 7-trifluoromethylimidazo[1,2-a]pyrimidine (5) to 5?-chloro-4,2?-difluorobiphenyl-2-carbonitrile (15). The efficiency of this step was affected by the choice of solvent, ligand, and tetrabutylammonium salt additive.

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

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The invention relates to novel compounds containing one or more units derived from 1,5-disubstituted-1,5-dihydro-[1,5]naphthyridine-2,6-dione, to methods for their preparation and educts or intermediates used therein, to mixtures and formulations containing them, to the use of the compounds, mixtures and formulations as organic semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices and organic photodetectors (OPD), and to OE, OPV and OPD devices comprising these compounds, mixtures or formulations.

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

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The Buchwald-Hartwig amination allows an efficient and convenient synthesis of biologically and pharmaceutically important acridones by formation of a six-membered ring. With the described method, a number of derivatives have been synthesized in up to 95% yield by using a variety of anilines as well as benzylic and aliphatic amines.

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

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We report here our latest discovery on the directed lithiation and palladium-catalyzed arylation of anisoles. During this research, the formation of a four-membered lithiumcycle followed by transmetalation to the corresponding palladacycle has been achieved, which is difficult to be obtained from palladium-catalyzed C-H activation processes. This approach has provided an alternative way of introducing functionalities to arenes such as anisoles, thioanisoles, and anilines. This approach also features an excellent monoselectivity compared with reactions under transition-metal-catalyzed conditions.

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

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This review article gives an overview of past and current activities in the Linear Conjugated Systems Group of Angers and in the IPOC ? Functional Polymers Group of the Institute of Polymer Chemistry of Stuttgart on the use of triphenylamine (TPA) as versatile building block for organic electronics. In the first part, the properties of TPA itself are introduced including geometrical and energy level considerations. Dimerization of TPA to tetraphenylbenzidine upon electrochemical oxidation is highlighted. The blocking of TPA para-positions and its implications in terms of electroactivity is further discussed. The second part shows that dimerization of TPA as pendant redox-active moieties in polymers is a versatile strategy to crosslink polymer films. Coming from redox homopolymers the crosslinking strategy is extended towards conjugated redox polymers based on polythiophenes and block copolymers. Conductivity mechanisms and the influence of doping level on conductivity are probed with cyclic voltammetry coupled with in situ conductance and four-point probe measurements. The last part is dedicated to the use of TPA as an electron-donating block in the design of donor-pi-acceptor chromophores and their use as active material in organic photovoltaics. An overview of some relevant TPA-based push?pull molecules from the literature and our contribution to this field is presented emphasizing the progress of the photovoltaic performance of organic solar cells made over the last decade.

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

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Two novel thiadiazoloquinoxaline and benzodithiophene (BDT) bearing copolymers were designed and synthesized. Different BDT units (alkoxy and thiophene substituted) were used as donor materials and the effect of alkoxy and thiophene substitution on the electrochemical, spectroelectrochemical and photovoltaic properties were investigated. Both polymers exhibited low oxidation potentials at around 0.90 V and low optical band gaps at around 1.00 eV due to the insertion of electron poor thiadiazoloquinoxaline unit into the polymer backbone. Both P1 (poly-6,7-bis(3,4-bis(decyloxy)phenyl)-4-(4,8-bis(nonan-3-yloxy)benzo[1,2-b:4,5-b’]dithiophen-2-yl)-[1, 2, 5]thiadiazolo[3,4-g]quinoxaline) and P2 (poly- 4-(4,8-bis(5-(nonan-3-yl)thiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophen-2-yl)-6,7-bis(3,4-bis(decyloxy)phenyl)-[1, 2, 5]thiadiazolo[3,4-g]quinoxaline) exhibited multichromic behavior with different tones of greenish yellow and gray in the neutral and fully oxidized states, respectively. In addition, both polymers revealed very high optical contrasts (?87%) in the NIR region which make these promising polymers good candidates for NIR applications. Finally, in order to explore the organic photovoltaic performances, P1 and P2 were mixed with PC71BM in the active layer of organic solar cells (OSCs) by conventional device structure. As a result P1 and P2 based devices revealed power conversion efficiencies (PCEs) of 0.33% and 0.60% respectively. However, the additive treatment enhanced PCE from 0.49 to 0.73% for P2 based devices.

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

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Pd-catalyzed hydroalkynylations were developed that involve ligand-enabled regiodivergent addition of an alkyne to an allenamide, giving branched and linear products stereoselectively and facilitated by the neighboring amide group. Regioselectivity was achieved with the use of (o-OMePh)3P and BrettPhos, which allowed the functionalization of various alkynes, including steroids, carbohydrates, alkaloids, chiral ligands, and vitamins. Based on the experimental results, it was proposed that hydro- and carbopalladation processes operated during the formations of the branched and linear products, respectively.

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

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The invention relates to a kind of oxazole and quinoline compounds and its preparation method, its preparation method is as follows: the formula (I) of the alkyne base key is joint of the azido compound with the nitrile compounds to R ‘ CN M metal catalyst under the action of the reaction, the reaction temperature is – 40 C -80 C, after the reaction is complete to obtain the […] and quinoline compound; wherein reaction are as follows: Wherein Ar selected from aromatic group or substituted aromatic group; R is selected from the aromatic group, substituted aromatic group, alkyl or substituted alkyl; R ‘ is selected from alkyl, substituted alkyl, substituted alkenyl, aromatic group or substituted aromatic group. The invention provides oxazole and in the quinoline compound containing pyridine and oxazole pharmocology, has very good biological activity, can be used as the chemical or pharmaceutical intermediates. (by machine translation)

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

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Efficient synthetic strategies for furnishing alpha-carbolines have been developed by integrating various Pd-catalyzed reactions. The methods involve 1) regioselective 5- or 6- halogenation of alpha-carbolines which were synthesized through intramolecular Pd-catalyzed direct C-H arylation, and subsequent Pd-catalyzed cross coupling, 2) 8-triflation of alpha-carbolines constructed by Pd-catalyzed cyclization, followed by Pd-catalyzed cross-coupling reaction, 3) Pd-catalyzed cyclization to tetrahydro-alpha-carbolines and subsequent Suzuki reaction via the corresponding alpha-carboline 5-triflates.

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Reference:
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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A novel alternating copolymer with benzo[1,2-b:4,5-b?]dithiophene as electron-rich unit and fluorinated phenanthrenequinoxaline segment as electron-withdrawing unit was synthesized. The polymer showed a low-lying highest occupied molecular orbit energy level of -5.34 eV with a very low bandgap of 1.53 eV. Solar cell devices were fabricated by using the polymer as donor and [6,6]-phenyl-C71-butyric acid methyl ester as acceptor, respectively. The photovoltaic properties were studied and power conversion efficiency of 1.90% was obtained with an open-circuit voltage of 0.72 V for an optimal donor/acceptor weight ratio of 1:2 with 3% 1,8-diiodooctane. These results demonstrated that fluorine substituted phenanthrenequinoxaline based D-A conjugated polymer might be promising materials for bulk heterojunction photovoltaic cells.

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