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Desulfinylative Pd-catalyzed coupling reaction of arenediazonium salt with aryl sulfinates to give unsymmetrical biaryls

An efficient route for the synthesis of unsymmetrical biaryls was developed via palladium catalyzed reaction of arenediazonium salts and aryl sulfinates under inert atmosphere. This synthesis involves cascade processes. Tetrabutylammonium iodide was used as an iodide source for in situ formation of aryl iodide, followed by desulfinylative cross-coupling reaction between aryl sulfinates and aryl iodides. A wide range of biaryls were selectively prepared in one pot from simple substrates in good to excellent yields.

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

Final Thoughts on Chemistry for 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex

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Pd(0) – MEDIATED CROSS-COUPLING OF REFORMATSKY REAGENTS WITH VINYL- AND ARYL TRIFLATES.

Pd(0) – Mediated cross-coupling reaction between Reformatsky reagents and vinyl/aryl triflates is reported.The method represents a procedure for the synthesis of beta-gamma unsaturated esters and aryl acetic esters.

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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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Cycloalkane Derivatives

Disclosed herein are therapeutic agents and/or preventive agents for pain or therapeutic agents and/or preventive agents for a sodium channel associated disease. The present invention provides compounds represented by the following formula (I) or pharmacologically acceptable salts thereof:

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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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Synthesis, X-ray, spectroscopic and a preliminary Suzuki coupling screening studies of a complete series of dppfMX2 (M=Pt, Pd; X=Cl, Br, I)

A complete series of dppfMX2 (M=Pt, Pd; X=Cl, Br, I) compounds have been synthesized using different routes, and characterized fully. The synthesis of dppfPdI2 has been achieved by reacting Pd(COD)Cl2 with dppf in the presence of NaI. X-ray structures of dppfPdBr2 and dppfPdI2 have also been reported for the first time in this study. A preliminary Suzuki coupling screening study reveals that dppfPdX2 compounds are superior to the conventional Ph3P-based catalysts and bidentate phosphine-based ligands. Reactions carried out under in situ conditions also gave a similar trend, but their respective activities were much lower than that of the fully formed catalysts.

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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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Palladium-catalyzed C-C bond formation to construct 1,4-diketones under mild conditions

Palladium can do it! A novel palladium-catalyzed reaction between the bulky alpha-carbon centers of two ketones has led to the construction of 2,3-diaryl-1,4-diketones by employing alpha-chloroketones as electrophiles and zinc ketone enolates as nucleophiles (see scheme). This reaction allows the synthesis of bulky 1,4-diketones and is complementary with classic nucleophilic substitution reactions. Copyright

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

Extended knowledge of 95464-05-4

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Synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate and its application in the synthesis of 4-(aryl/heteroaryl/alkynyl)phthalazin-1(2H)-one

The regioselective synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate (3a) has been reported. The reaction of Tf2O (2a) with phthalhydrazide (1a) provides a rapid access to 3a with an excellent yield and a high level of regioselectivity. The synthetic utility of this triflate is further enhanced by carrying out the successful Suzuki and Sonogashira coupling reactions for the first time on 3a, providing a simple access to a range of biologically significant 4-aryl/heteroaryl/alkynyl phthalazinones in good yields.

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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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New acetonyl palladium(II) complexes

[Pd(CH2C(O)Me)Cl]n (1), reacts with P- and N-donor ligands to afford cis-[Pd{CH2C(O)Me}Cl(dppf)] (dppf = bis(diphenylphosphino)ferrocene (2)) and [Pd(CH2C(O)Me)ClL 2] (L = pyridine = py (3), 4-Me-pyridine = Mepy (4), 4- tBu-pyridine = tBupy (5)). Reaction of 3 or 3-5 with 1 equiv of [Tl(acac)] or TlTfO and L affords, respectively, [Pd(CH 2C(O)Me}(O,O-acac)(py)] (6) or [Pd(CH2C(O)Me)L 3]TfO (L = py (7), Mepy (8), tBupy (9)). The reaction of 9 with 1 equiv of (Ph2P(CH2)2}2PhP (triphos) gave [Pd{CH2C(O)Me}(triphos)]TfO (10). Complex 1 reacts with norbornene (nbn) followed by addition of L2 (1:2:1), with 1,5-cyclooctadiene (cod) (1:1) or with 1, 1-dimethyl aliene (dma) to give [Pd{(nbn)-CH2C(O)Me)ClL2] (L2 = 2,2?-bipyridine (bpy) (11), 4,4?-di-tert-butyl 2,2?-bipyridine (dbbpy) (12)), [Pd(CH2C(O)Me]Cl(cod)] (13), or [Pd(eta 3-CH2C(CH2C(O)Me]Cl]2 (14), respectively. The structures of complexes 3, 8, 11, and 13 have been solved by X-ray diffraction studies.

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

Archives for Chemistry Experiments of 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex

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Multistep solid-state organic synthesis of carbamate-linked covalent organic frameworks

Herein, we demonstrate the first example of a multistep solid-state organic synthesis, in which a new imine-linked two-dimensional covalent organic framework (COF-170, 1) was transformed through three consecutive postsynthetic modifications into porous, crystalline cyclic carbamate and thiocarbamate-linked frameworks. These linkages are previously unreported and inaccessible through de novo synthesis. While not altering the overall connectivity of the framework, these chemical transformations induce significant conformational and structural changes at each step, highlighting the key importance of noncovalent interactions and conformational flexibility to COF crystallinity and porosity. These transformations were assessed using 15N multiCP-MAS NMR spectroscopy, providing the first quantitation of yields in COF postsynthetic modification reactions, as well as of amine defect sites in imine-linked COFs. This multistep COF linkage postsynthetic modification represents a significant step toward bringing the precision of organic solution-phase synthesis to extended solid-state compounds.

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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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A divergent strategy to the withasomnines

A concise synthesis of three members of the withasomnine family of natural products is reported. The synthesis features a regioselective sydnone-alkynylboronate cycloaddition followed by Suzuki cross coupling and silyl group removal, and marks the first divergent approach to this family of pyrazole based natural products.

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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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Synthesis of Electron-Deficient Heteroaromatic 1,3-Substituted Cyclobutyls via Zinc Insertion/Negishi Coupling Sequence under Batch and Automated Flow Conditions

Synthesis of 1,3-substituted cyclobutyls enabled by zinc insertion into functionalized iodocyclobutyl derivatives followed by Negishi coupling with halo-heteroaromatics is reported. Two distinct sets of conditions were developed; the first involved a two-step batch protocol using activated Rieke zinc, and the second involved a multistep continuous flow process. Both methods showed complementarity and allowed for rapid access to these medicinally relevant motifs, the possibility of scaling up, and automation for library synthesis.

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