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A palladium/norbornene cooperative catalysis to access N-containing bridged scaffolds

A palladium/norbornene cooperative catalysis promoted annulation involving an ortho-C-H amination and intramolecular Heck cascade between aryl iodides and functionalized amination reagents is reported, thereby providing a highly convergent access to the unique N-containing bridged scaffolds: hexahydro-2,6-methano-1-benzazocine. The salient features of the reaction include its broad substrate scope (with respect to aryl iodides), its high step economy, and good chemoselectivity. Preliminary studies underscore the future promise of rendering this Catellani-type annulation enantioselective.

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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 Regioselective Allylation of Chloromethyl(hetero)arenes with Allyl Pinacolborate

The palladium-catalyzed regioselective allylation reaction between chloromethyl(hetero)arenes and allyl pinacolborate is reported in this work. Chloromethylarenes smoothly reacted with allyl pinacolborate, producing para-allylated dearomatization products or para-allylated arenes in satisfactory to good yields. 2-(Chloromethyl)thiophenes and 2-(chloromethyl)furans bearing substituents on the 5-positions also smoothly reacted with allyl pinacolborate, producing the 5-allylated dearomatization products in satisfactory yields. (Figure presented.).

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

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Organopalladium complexes of oxacalixarenes: Selecting the lid for the three-dimensional scaffold

The first organometallic (palladium) complexes of oxacalixarene molecules were prepared via oxidative addition of the C-I bond at the lower rim. The unique geometry of the oxacalixarene scaffold allowed for the selective introduction of new ligands at the top of the calixarene scaffold. Such coordination can be used to coordinatively link the opposing aromatic rings.

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

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ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

A compound comprising a ligand LA of Formulae I, II, or III wherein the ligand LA is coordinated to a transition metal M, and optionally, M is also coordinated to a ligand LB; A is N, B, or CR7; Y is absent, or selected from the group consisting of C(O), C(Rya)(Ryb), C?C(Rya)(Ryb), and Si(Rya)(Ryb), where if Y of Ring A is absent then ring carbon of R2 is bonded to N; wherein for the compounds of formula III at least one of R2, R3, and R4 is selected from N(Ar1)RN? or aryloxy; wherein Ar1 is selected from aryl or heteroaryl, each of which is optionally substituted. An OLED that includes an organic layer disposed between an anode and a cathode, and the organic layer includes a compound comprising a ligand LA of Formulae I, II, or III above. The OLED can be incorporated into one or more of a consumer product, e.g., an electronic component module, a flat panel display, e.g., a display for a phone, television, laptop, and/or a lighting panel for either commercial or residential applications.

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

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COMPOUND

The present invention relates inter alia to a compound of formula (I) and to compositions comprising the same and to the use of the compounds and to compositions of the compounds in treatment, for example in the treatment of inflammatory diseases, in particular respiratory inflammatory disease. The invention also extends to methods of making the said compounds.

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

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Preparation of 1,5-Dihydropyrazolo[3?,4?:5,6]pyrano[3,4- b]pyridines via a Microwave-Assisted, Palladium-Catalyzed Regioselective C-H Heteroarylation of Electron-Rich Pyrazoles

Here we report the first synthesis of a family of novel heterocyclic compounds based on a 5-dihydropyrazolo[3?,4?:5,6]pyrano[3,4-b]pyridine core. In the course of our drug discovery programs, we had need to access the previously unknown 5-dihydropyrazolo[3?,4?:5,6]pyrano[3,4-b]pyridine core. Initial attempts required long reaction times, which led to degradation and side products. Reaction optimization identified a Pd-catalyzed, microwave-assisted C-H heteroarylation protocol for the rapid, general, and high yielding synthesis of this tricyclic core (as well as related analogs) suitable to drive optimization efforts.

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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 synthesis of chiral heterocyclic biaryls via asymmetric Suzuki-Miyaura cross-coupling of 3-bromopyridine derivatives

A series of chiral heterocyclic biaryls with a pyridyl moiety were prepared in moderate to good yields with up to 92% ee via asymmetric Suzuki-Miyaura coupling. The chiral-bridged biphenyl monophosphine ligand L1 was found to be much more effective in the reaction enantioselection than its counterpart binaphthyl monophosphine ligands.

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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 N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C?N Cross-coupling

A number of beta-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding beta-diketones. Two general protocols for their palladium-catalyzed intramolecular C?N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

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

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NOVEL PYRAZOLE DERIVATIVE

It has been desired to develop a pharmaceutical composition, which is used in agents for preventing and/or treating various diseases related to PDE10 (e.g. mental disorder and neurodegenerative disorder). The present invention provides: compounds having PDE10 inhibitory effect, in particular, compounds having a 4-heteroarylpyrazole-5-carboxylic acid amide structure represented by the following formula (I), or their pharmaceutically acceptable salts, or their solvates; pharmaceutical compositions comprising, as active ingredients, the compounds, or their pharmaceutically acceptable salts, or their solvates; and medical use of the compounds, or their pharmaceutically acceptable salts, or their solvates.

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

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Auto-tandem catalysis: Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling

A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C-N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized acridine derivatives, which are generally difficult to synthesize by previously known methods.

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