Some scientific research about Pd2(DBA)3

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Barbier?Negishi Coupling of Secondary Alkyl Bromides with Aryl and Alkenyl Triflates and Nonaflates

A mild and practical Barbier?Negishi coupling of secondary alkyl bromides with aryl and alkenyl triflates and nonaflates has been developed. This challenging reaction was enabled by the use of a very bulky imidazole-based phosphine ligand, which resulted in good yields as well as good chemo- and site selectivities for a broad range of substrates at room temperature and under non-aqueous conditions. This reaction was extended to primary alkyl bromides by using an analogous pyrazole-based ligand.

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

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Synthesis, structure-activity relationship studies, and identification of novel 5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine derivatives as dual orexin receptor antagonists. Part 1

A novel series of non-peptidic OX1R/OX2R orexin receptor antagonists was prepared by heterocyclic replacement of the dimethoxyphenyl moiety contained in the tetrahydroisoquinoline core skeleton of almorexant. Introduction of substituted imidazole moieties delivered potent dual orexin receptor antagonists with nanomolar potency for hOX1R and hOX2R suitable for further fine-tuning. The preparation of these novel orexin receptor antagonists and the outcome of preliminary structure-activity relationship studies are described in this communication.

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

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Enantioselective Coupling of Dienes and Phosphine Oxides

We report a Pd-catalyzed intermolecular hydrophosphinylation of 1,3-dienes to afford chiral allylic phosphine oxides. Commodity dienes and air stable phosphine oxides couple to generate organophosphorus building blocks with high enantio- and regiocontrol. This method constitutes the first asymmetric hydrophosphinylation of dienes.

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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 Thiophene-Aryl Coupling Reaction via C-H Bond Activation in Deep Eutectic Solvents

Direct arylation of 5-octylthieno[3,4-c]pyrrole-4,6-dione with a series of functionalized aryl iodides via C-H bond activation is demonstrated in a deep eutectic solvent made of choline chloride and urea in non-anhydrous conditions and without exclusion of air. This is the first demonstration of a thiophene-aryl coupling via direct arylation in deep eutectic solvents.

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

Discovery of Pd2(DBA)3

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Palladium nanoparticles in glycerol: A versatile catalytic system for C-X bond formation and hydrogenation processes

Palladium nanoparticles stabilised by tris(3-sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in C-X bond formation processes (X=C, N, P, S) and C-C multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as-prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular- and surface-like behaviour), has allowed attractive applications in one-pot multi-step transformations catalysed by palladium, such as C-C coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor. Copyright

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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 Stereoselective 1,2-Aryboration of Alkenylarenes

The palladium-catalyzed highly regio- and diastereoselective arylboration of alkenylarenes has been developed. This chemistry afforded the benzylic boronic esters with a broad substrate scope, which are valuable synthetic intermediates for organic synthesis. The chiral anion phase-transfer strategy was designed for this transformation to realize the regio-, diastereo-, and enantioselective control of this reaction simultaneously.

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

Extended knowledge of Pd2(DBA)3

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[1,2,4] TRIAZOLO [4,3-B] PYRIDAZINE COMPOUNDS AS INHIBITORS OF THE C-MET TYROSINE KINASE

The invention relates to compounds of formula (I) and salts thereof: wherein the substituents are as defined in the specification; a compound of formula (I) for use in the treatment of the human or animal body, in particular with regard to c-Met tyrosine kinase mediated diseases or conditions; the use of a compound of formula (I) for manufacturing a medicament for the treatment of such diseases; pharmaceutical compositions comprising a compound of the formula (I), optionally in the presence of a combination partner, and processes for the preparation of a compound of formula (I).

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

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Palladium-mediated 11C-carbonylations using aryl halides and cyanamide

A robust and high-yielding radiochemical synthesis of 11C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with 11C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1?-bis(diphenylphosphino)ferrocene provided 11C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28-79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel 11C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34-71% radiochemical yields.

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

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Synthesis of regiocontrolled triarylamine-based polymer with a naphthol unit

Redox-active polytriarylamine with hydroxyl groups is a useful material for optoelectronic applications, especially in the solution-processable multilayer devices. A novel regiocontrolled triarylamine-based polymer, poly(di-5-naphthyl-2-ol)phenylamine, with 2-naphthol units was synthesized via oxidative coupling polymerization. Polymerization in tetrahydrofuran using a Cu-amine complex oxidant under O2 atmosphere produced polymers with number-averaged molecular weights as high as 11,300 g mol?1. The structure of the polymer was characterized by 1H and 13C NMR spectroscopy, showing that the oxidative coupling polymerization occurred at the outer ortho position of the 2-naphthols, preserving the hydroxyl groups. The polymer exhibited good solubility in polar aprotic solvents, with a high thermal stability of 446 C that corresponded to 5% weight loss. The UV?vis absorption of the polymer was similar to that of DNPA, indicating that the kinked-structured polymer hindered the formation of charge-transfer complexes. These results suggest promising applications of the developed polymer in optoelectronic 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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Palladium-Catalyzed Asymmetric Allylic Alkylations of Colby Pro-Enolates with MBH Carbonates: Enantioselective Access to Quaternary C?F Oxindoles

Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C?F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an SN2 reaction catalyzed by Pd/Ding-SKP-type ligands, and that occurs between Colby pro-enolates with MBH carbonates to afford the corresponding products featuring two consecutive stereogenic carbons, including a C?F quaternary stereogenic center. The reactions readily occur at ambient temperatures with high chemical yields and in excellent chemo-, diastereo- and enantioselective manners. This practically attractive stereochemical outcome, coupled with the operational simplicity and structural generality, bodes well for the synthetic application of this process in the preparation of a novel class of biologically relevant fluorine-containing compounds.

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