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Methyl 2-furoate: An alternative reagent to furan for palladium-catalysed direct arylation

The palladium-catalysed direct arylation of methyl 2-furoate with aryl bromides was studied. The use of KOAc as the base, dimethylacetamide (DMAc) as the solvent and Pd(OAc)2 as the catalyst was found to give 5-arylfurans regioselectively and without decarboxylation. These methyl 5-aryl-2-furoates gave 2,5-diarylfurans by decarboxylative coupling by using Pd(OAc)2 as the catalyst. Methyl 2-furoate thus represents a convenient alternative substrate to furan for the synthesis of mono- or poly-arylated furans.

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Formal N-acylation reaction of azaaromatics with acylzirconocene chloride complexes and 1,1,1,3,3,3-hexafluoro-2-propanol

In the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (1,1,1,3,3,3-hexafluoroisopropyl alcohol, HFIP), isoquinolines react with acylzirconocene chlorides to give N-acyl adducts with incorporation of a proton at the C-1 position. The present procedure could be applied to the reaction of quinolines. These reactions provide us with an alternative method for the Reissert-type reduction reactions of azaaromatics with N-acylating reagents and reducing reagents.

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Hydrosilyl Group-directed Iridium-catalyzed peri-Selective CH Borylation of Ring-fused (Hetero)Arenes

The iridium-catalyzed direct CH borylation of ring-fused (hetero)arenes afforded borylated products in a peri-selective manner, directed by a proximal hydrosilyl group. Further selective transformations of the boryl and silyl groups enabled the synthesis of various multisubstituted (hetero)arenes, such as 1,8-disubstituted naphthalenes and 3,4-diarylindole.

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Intermolecular versus Intramolecular Palladium-Catalyzed Direct Arylations between 1-(2-Bromobenzyl)imidazoles and Aryl Bromides

Herein, we report on the sequential palladium-catalyzed intermolecular followed by intramolecular direct arylations of 1-(2-bromobenzyl)imidazoles. We found that, in the presence of 1 mol% palladium acetate and potassium acetate as base, the intermolecular reaction between 1-(2-bromobenzyl)imidazole derivatives and electron-deficient aryl bromides proceeded faster than the intramolecular reaction, allowing us to prepare medium-size polycyclic imidazoles after a second Pd-catalyzed intramolecular arylation. These iterative direct arylations allowed the synthesis of fused nitrogen-containing heterocycles with a 5- or 7-membered-ring in only two steps. Some reactions have also been performed as a one-pot procedure using 2 mol% of palladium acetate in the presence of a larger amount of base (3 equiv.).

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Isoquinoline – Wikipedia,
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Modification of silica using piperazine for immobilization of palladium nanoparticles: A study of its catalytic activity as an efficient heterogeneous catalyst for Heck and Suzuki reactions

An efficient heterogeneous palladium catalyst system has been developed based on immobilization of Pd nanoparticles on silica-bonded N-propylpiperazine (SBNPP) substrate. SBNPP substrate can stabilize the Pd nanoparticles effectively so that it can improve their stability against aggregation. Also, grafted piperazine species onto the silica backbone prevents the removing of Pd nanoparticles from the substrate surface. It seems that the high recyclable capability of Pd-SBNPP catalysts is resulted from these two characteristics. Transmission electron microscopy (TEM) of catalyst is shown the size of Pd nanoparticles in Pd-SBNPP average of 20 nm. Furthermore, X-ray photoelectron spectroscopy (XPS) of Pd-SBNPP is shown the presence of Pd(0) in the structure of this catalyst. Overall, TEM, XPS and XRD experiments strongly suggested that Pd nanoparticles were formed and immobilized on silica-functionalized piperazine. The catalytic activity of this catalyst was investigated in the Heck and Suzuki reactions. The catalyst could be recycled several times without appreciable loss in catalytic activity.

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Isoquinoline – Wikipedia,
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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 1532-97-4, name is 4-Bromoisoquinoline, introducing its new discovery. category: Isoquinolines

Scope of the Suzuki-Miyaura aminoethylation reaction using organotrifluoroborates

(Chemical Equation Presented) Potassium beta-aminoethyltrifluoroborates were prepared in good yields via hydroboration of the corresponding enecarbamates using the Snieckus hydroborating reagent. A wide variety of phenethylamines containing a potentially free primary amine after appropriate deprotection have been successfully prepared in good yield using these organotrifluoroborates as partners in Suzuki-Miyaura coupling with aryl bromides, iodides, and triflates.

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NITROGENEOUS TRICYCLIC COMPOUND

A novel compound represented by the following formula (1) [wherein R1, R5, R6, R7, and R8 each represents hydrogen, halogeno, hydroxy, alkyl, alkenyl, etc.; X1¡¤¡¤¡¤X2 represents -CH(R2)-CH(R3)-, -CH(R2)-CH(R3)-CH(R4)-, -C(R2)=C(R3)-, or -C(R2)=C(R3)-CH(R4)- (R2, R3, and R4 each represents hydrogen or alkyl); A1, A11, A2, and A21 each represents hydrogen or alkyl; Y represents -CH(A3)-, -CH(A3)-C(A4)(A41)-, -CH(A3)-C(A4)(A41)-C(A5)(A51)-, or a single bond (A3, A4, A41, A5, and A51 each represents hydrogen or alkyl); and Z represents hydroxy or -N(A6)(A61) (A6 represents hydrogen or alkyl and A61 represents hydrogen, alkyl, substituted alkyl, etc.)] or a salt of the compound. The compound has the potent ability to inhibit the phosphorylation of a myosin light chain. [Chemical formula 1]

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Isoquinoline – Wikipedia,
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Efficient homo-coupling reactions of heterocyclic aromatic bromides catalyzed by Pd(OAc)2 using indium

Homo-coupling reactions of heterocyclic aromatic bromides smoothly proceeded with cat-Pd(OAc)2, indium, and LiCl in DMF to afford exclusively symmetric biaryls possessing heterocyclic aromatic ring in good to excellent yields.

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Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium-tetraphosphine complex

Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane / 0.5 [PdCl(C3H5)]2 system catalyses the Heck reaction of vinylsilane derivatives with a range of aryl bromides with high ratio substrate/catalyst in good yields. The formation of mixtures of styrene, (E)-triethyl(2-arylethenyl)silane and triethyl(1-arylethenyl)silane derivatives was observed in some cases. Very high selectivities (up to 100%) in favour of the formation of (E)-triethyl(2-arylethenyl)silane derivatives were obtained in the presence of sodium acetate as base. With other bases such as potassium carbonate, the formation of large amounts of styrene derivatives was observed. The reaction tolerates several functions such as fluoro, trifluoromethyl, methoxy, dimethylamino, acetyl, formyl, benzoyl, carboxylate, nitro or nitrile. Moreover, turnover numbers up to 10,000 can be obtained for this reaction.

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Novel indolylindazolylmaleimides as inhibitors of protein kinase C-beta: Synthesis, biological activity, and cardiovascular safety

Novel indolylindazolylmaleimides were synthesized and examined for kinase inhibition. We identified low-nanomolar inhibitors of PKC-beta with good to excellent selectivity vs other PKC isozymes and GSK-3beta. In a cell-based functional assay, 8f and 8i effectively blocked IL-8 release induced by PKC-betaII (IC50 = 20-25 nM). In cardiovascular safety assessment, representative lead compounds bound to the hERG channel with high affinity, potently inhibited ion current in a patch-clamp experiment, and caused a dose-dependent increase of QTc in guinea pigs.

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