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Nano palladium supported on high-surface-area metal-organic framework MIL-101: An efficient catalyst for Sonogashira coupling of aryl and heteroaryl bromides with alkynes

Palladium nanoparticle-incorporated metal-organic framework MIL-101 (Pd/MIL-101) was successfully synthesized and characterized using X-ray diffraction, nitrogen physisorption, X-ray photoelectron, UV-visible and infrared spectroscopies, and transmission electron microscopy. The characterization techniques confirmed high porosity and high surface area of MIL-101 and high stability of nano-size palladium particles. Pd/MIL-101 nanocomposite was investigated for the Sonogashira cross-coupling reaction of aryl and heteroaryl bromides with various alkynes under copper-free conditions. The reusability of the catalyst was tested for up to four cycles without any significant loss in catalytic activity.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H3001N – PubChem

 

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NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H3060N – PubChem

 

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Copper-catalyzed cyanation of heteroaryl bromides: A novel and versatile catalyst system inspired by nature

An improved copper catalyst system for the cyanation of heteroaryl halides leading to substituted heteroaryl nitriles is described. The catalyst system consists of simple CuI and N-alkylimidazoles, and mimics known Cu-containing metalloproteins. It is stable, commercially available, cheap and easily tunable. By using inexpensive and non-toxic K4[Fe(CN)6] and the novel Cu catalysts we were able to cyanate both activated and non-activated heteroarenes with high yield and selectivity. The generality of the procedure is demonstrated by a variety of different examples, some of which did not react under other known methods. Georg Thieme Verlag Stuttgart.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H3347N – PubChem

 

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Acetylene-free synthesis of vinyloxy pyridine and quinoline

Copper-catalyzed vinylation of 2- and 4-hydroxy pyridine and quinoline affords exclusively N-vinylation products. However, vinyl ethers of 4-hydroxy pyridine and quinoline can be prepared via a three-step sequence involving copper-catalyzed C-O cross coupling reaction of the corresponding N-heteroaryl bromides with ethylene glycol, chlorination of the terminal alcohol, and dehydrohalogenation of the beta-chloro ethers. Although not efficient in 2-hydroxy series, this method can be conveniently applied to the preparation of various aza-aryl vinyl ethers in moderate to good overall yields.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H3142N – PubChem

 

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Allylboration of functionalized isoquinolines

Functionalized isoquinolines react with triallylborane to produce 1,3-diallylated 1,2,3,4-tetrahydroisoquinolines 1-8 with excellent chemo- and stereoselectivity. In these conditions 4-bromoisoquinoline was converted into tricyclic aziridine 10. Synthesis of monoallylated tetrahydroisoquinolines using allyldipropylborane and reduction with NaBH4 was also developed.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H3312N – PubChem

 

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Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium-tetraphosphine complex

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)- cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords a very efficient catalyst for the coupling of cyclopropylboronic acid with aryl bromides and aryl chlorides. Higher reactions rates were observed with aryl bromides than with aryl chlorides; however, even in the presence of 1-0.4% of catalyst, a few aryl chlorides gave the coupling products in good yields. A wide variety of substituents such as alkyl, methoxy, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, and nitrile on the aryl halides are tolerated. The coupling reaction of sterically very congested aryl bromides such as bromomesitylene or 2,4,6-triisopropylbromobenzene also proceeds in good yields. Copyright Taylor & Francis LLC.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H3214N – PubChem

 

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Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis

Detailed in this Communication is the enantioselective synthesis of 1,1-diarylalkanes, a structure found in a range of pharmaceutical drug agents and natural products, through the employment of copper(I) hydride and palladium catalysis. Judicious choice of ligand for both Cu and Pd enabled this hydroarylation protocol to work for an extensive array of aryl bromides and styrenes, including beta-substituted vinylarenes and six-membered heterocycles, under relatively mild conditions.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H3117N – PubChem

 

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Decahydro-isoquinolines

1 The invention provides compounds of formula (I), wherein A, B and R are as defined in the description, and the preparation thereof. The compounds of formula (I) are useful as somatostatin receptor antagonists.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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An organocatalyst bound alpha-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions

A catalyst bound alpha-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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A facile, microwave-assisted, palladium-catalyzed arylation of acetone

We report an expedient method for the heteroarylation of acetone under tin-free conditions. The coupling is performed using the commercially available enol silane of acetone (2-trimethylsilyloxypropene) and a corresponding aryl bromide, chloride or triflate under microwave-assisted conditions, with tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) or palladium acetate (Pd(OAc)2) and 2-(2?,6?-dimethoxybiphenyl)dicyclohexylphosphine (S-Phos) as the catalyst system.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem