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A wide range of catalysts based on supported copper nanoparticles have been prepared and tested in the cross-dehydrogenative coupling of tertiary amines and terminal alkynes. Copper nanoparticles on zeolite Y were found to be the most effective catalyst in the presence of tert-butyl hydroperoxide as the oxidant. Contrary to the previously reported methodologies involving copper catalysts, reactions have been accomplished without the need of an inert atmosphere and in the absence of solvent, using 1.5mol% catalyst. A variety of tertiary amines, including aromatic, benzylic and aliphatic ones, have been coupled with both aromatic and aliphatic alkynes to furnish the corresponding propargylamines in moderate-to-excellent yields. The procedure has been successfully scaled-up to 12mmol with a high conversion (93%). Moreover, the catalyst has been reused in seven cycles maintaining a good performance. Its catalytic activity has been compared with that of an array of commercial copper catalysts, being superior as regards the conversion and minimizing the alkyne homocoupling as a side reaction. The negative filtration test points to a heterogeneous nature of the process. Based on compelling experimental evidence, a novel reaction mechanism has been delineated which outlines the essential role of free radicals and the couple copper(I)/copper(II).

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

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Molybdenum trioxide (MoO3) catalyzed efficient oxidative cross-dehydrogenative-coupling (CDC) method for C-H functionalization of N-aryl tetrahydroisoquinolines has been explored. This user-friendly method of synthesizing alpha-aminophosphonates employs 1.1 equiv of dialkyl-H- phosphonate under aerobic condition. Formation of new C-P bonds from unfunctionalized starting materials under environmentally benign conditions provides an excellent avenue for the synthesis of biologically active alpha-aminophosphonates.

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

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The use of photon energy to promote chemical transformations offers versatile control of reaction kinetics and progress. Over the past decade, many photoactive transition-metal complexes and organic chromophores were developed to catalyze chemical transformations, enabling a myriad of reactions and compounds that were previously inaccessible via traditional synthetic methods. Here, we demonstrate the photocatalytic oxidative coupling of organic thiols using cesium lead halide perovskite nanocrystals as photocatalysts. The photo-catalyzed thiol coupling reactions selectively produced symmetric and unsymmetrical disulfides in high yields (68-96% isolated yields). Additionally, we discovered a perovskite-catalyzed phosphonylation of tertiary amines via visible-light-mediated cross-dehydrogenative coupling reaction, and obtained good isolated yields (50-96%). The variety of visible-light-induced photocatalytic processes that perovskite nanocrystals are capable of, coupled with their facile preparation, easily tunable redox potentials, high catalytic efficiency and reusability, presents great opportunities for their future applications in green and sustainable organic synthesis.

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

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The manufacturing method reel [thu [thu] high draw child small quinoline derivatives disclosure in the nanometer range. The present invention refers to, metal-based dye and visible light from high draw child small quinoline Mannich derivatives in high yield and short time in high draw child small quinoline (tetrahydroisoquinoline) 2 2 efficiently number can be characterized as having a high pressure liquid coolant. (by machine translation)

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

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Chemical Research Letters, May 2021. Synthetic Route 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 mild, selective, and efficient protocol for the synthesis of gamma-aminoalkyl butenolides via the oxidative coupling between tertiary amines and siloxyfurans catalyzed by simple copper salts was developed. Compared with the reported method, our method employs copper catalyst instead of the expensive rhodium catalyst. Besides TBHP, both O2 and H2O2 can also be utilized as oxidant to effect the coupling.

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

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New Advances in Chemical Research, May 2021. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis. Electric Literature of 3340-78-1, At least one of the reactants interacts with the solid surface in a physical process called adsorption in such a way. 3340-78-1, name is 2-Phenyl-1,2,3,4-tetrahydroisoquinoline. In an article,Which mentioned a new discovery about 3340-78-1

Development of cross-coupling chemistry by direct functionalization of C-H or heteroatom-H bonds under oxidative conditions proved to be ideal method for the construction of C-C and C-heteroatom bonds in recent times. Several transition metal catalysts were successfully utilized for these kind of transformations over the past several years. Among them, copper salts are of special importance because of their easy availability, biocompatibility and economical advantages. This review summarizes the current trends in Cu-catalyzed inter and intramolecular reactions under oxidative dehydrogenation process in achieving C-C, C-O, C-N, C-S and C-P bond formations over the past 3 years.

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

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A facile and efficient method to introduce alkyne groups to the C-1 position of biologically interesting 1,2,3,4-tetrahydroisoquinolines via direct C[sbnd]H-functionalization is reported. Various alkynylated N-substituted 1,2,3,4-tetrahydroisoquinolines could be obtained by using copper(I)-chloride as catalyst, alkynoic acids as alkyne source and t-BuOOH as oxidant, in a one-pot two-step decarboxylation- alkynylation reaction in moderate to high yields. Furthermore, a one-pot protocol of a three-step decarboxylation-alkynylation-1,3-dipolar cycloaddition reaction leading to 1-triazolyl-tetrahydroisoquinolines was developed, a hitherto unknown reaction cascade.

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

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The catalytic removal of a methoxy group on an aromatic ring allows this group to be used as a traceless activating and directing group for aromatic functionalization reactions. Although several catalytic methods for the reductive cleavage of anisole derivatives have been reported, all are applicable only to pi-extended aryl ethers, such as naphthyl and biphenyl ethers, while monocyclic aryl ethers cannot be reduced. Herein, we report a nickel-catalyzed reductive cleavage reaction of C-O bonds in aryl ethers using diisopropylaminoborane as the reducing agent. Unlike previously reported methods, this reducing reagent allows effective C-O bond reduction in a much wider range of aryl ether substrates, including monocyclic and heterocyclic ethers bearing various functional groups.

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

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A chemically functionalized nanocrystalline TiO2 grafted ruthenium(ii) polyazine complex was found to be an efficient visible light photoredox catalyst for the oxidative cyanation of tertiary amines to the corresponding alpha-aminonitriles in high to excellent yields, using molecular oxygen as an oxidant and sodium cyanide in acetic acid as a cyanide source. The developed photoredox catalyst could be easily recovered by simple filtration and reused for several runs with consistent catalytic activity.

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

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The benzoyl peroxide (BPO)-promoted oxidative functionalization of tertiary amines under transition-metal-free reaction conditions was developed. Various 1-trifluoromethylated tetrahydroisoquinoline derivatives were prepared by employing this method. It constitutes the first example of direct trifluoromethylation of tertiary amines.

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