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Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparations. In this paper, we report a direct cross-coupling reaction of indole with N-aryl tetrahydroisoquinolines in the presence of gold catalyst. The reaction is compatible with a wide range of substituted indoles, to enable the formation of various alkylated heteroarenes under very mild reaction conditions. Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparations. In this paper, we report a direct cross-coupling reaction of indole with N-aryl tetrahydroisoquinolines in the presence of gold catalyst. The reaction is compatible with a wide range of substituted indoles, to enable the formation of various alkylated heteroarenes under very mild reaction conditions. Copyright

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using alpha-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen.

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Porous cross-linked polymers (PCPs) with phosphorescent [Ru(bpy) 3]2+ and [Ir(ppy)2(bpy)]+ building blocks were obtained via octacarbonyldicobalt (Co2(CO) 8)-catalyzed alkyne trimerization reactions. The resultant Ru- and Ir-PCPs exhibited high porosity with specific surface areas of 1348 and 1547 m2/g, respectively. They are thermally stable at up to 350 C in air and do not dissolve or decompose in all solvents tested, including concentrated hydrochloric acid. The photoactive PCPs were shown to be highly effective, recyclable, and reusable heterogeneous photocatalysts for aza-Henry reactions, alpha-arylation of bromomalonate, and oxyamination of an aldehyde, with catalytic activities comparable to those of the homogeneous [Ru(bpy) 3]2+ and [Ir(ppy)2(bpy)]+ photocatalysts. This work highlights the potential of developing photoactive PCPs as highly stable, molecularly tunable, and recyclable and reusable heterogeneous photocatalysts for a variety of important organic transformations.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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Lately, the cross-dehydrogenative coupling of tetrahydroisoquinolines and nitroalkanes has become a widely studied reaction in organic chemistry; the corresponding beta-nitroamines are generally formed irrespective of the catalysis and activation mode utilized. A quite distinct behavior was observed when the reaction was catalyzed by copper nanoparticles supported on titania, leading to the formation of 5,6-dihydroindolo[2,1-a]isoquinolines with high selectivity and good yields. A meticulous reaction mechanism is proposed, based on experimentation, and discussed along with a key chemical modification of these compounds. Apparently, the catalyst effectiveness resides in its nanostructured character, outperforming the activity of the commercial copper catalysts.

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Chemical Research Letters, May 2021. Reference of 3340-78-1, The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.3340-78-1, Name is 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, molecular formula is C15H15N. In a Article,once mentioned of 3340-78-1

A visible-light photoredox catalyzed ring-opening functionalization of tetrahydroisoquinolines with bisindole alkylation has been developed, which expedites a new vista for the synthesis of bis(indolyl)methane derivatives. The transformation comprises a series of cascade reactions, photoredox catalysis, amine oxidation, fragmentation and Friedel?Craft alkylation. Five of the prepared bis(indolyl)methane derivatives containing the para substitution group on the side chain of benzene suppressed cancer cell growth in human breast adenocarcinoma MDA-MB-231 cells, and one candidate demonstrated a significant effect on cell migration.

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1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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A visible light mediated photocatalytic oxidative coupling reaction of N-phenyl tetrahydroisoquinoline with beta-keto acids has been developed. This approach provides a mild and operationally simple access to the synthesis of C1-acylmethylated tetrahydroisoquinolines.

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A redox-neutral reaction without using any external oxidant and reductant in one pot is described. By combining a Ru(bpy)32+ photocatalyst and cobaloxime catalyst, a number of tertiary anilines can be oxidized by Ru(bpy)32+ to realize oxidative cyclization of tetrahydroquinolines, and the electron and proton eliminated from the substrate anilines are captured by a cobaloxime catalyst to achieve hydrogen transfer in situ to maleimides, in good to excellent yields, under redox-neutral conditions.

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Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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A direct oxidative cross-dehydrogenative coupling (CDC) of N-aryl tetrahydroisoquinolins with 5H-oxazol-4-ones catalyzed by CuBr using air as the only oxidant has been developed, which could also proceed smoothly under a metal-free oxidative system with PhI(OAc)2 as the oxidant. A series of alkylated tetrahydroisoquinolin derivatives were obtained in good yields and excellent diastereoselectivities.

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Tetrahydroisoquinoline – Wikipedia,
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A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.

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Tetrahydroisoquinoline – Wikipedia,
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A convenient and efficient method for oxidative coupling of tetrahydroisoquinoline derivatives with trimethyl(trifluoromethyl)silane and terminal alkynes to 1-trifluoromethylated or 1-alkynylated tetrahydroisoquinolines via CH activation was developed using visible light irradiation. The protocol uses Rose Bengal as the catalyst, air as terminal oxidant, and the trifluoromethylation or alkynylation was selectively performed at the alpha-position of nitrogen under extremely mild conditions.

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