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Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

Reported herein is an unprecedented photocatalytic asymmetric cross-dehydrogenative coupling reaction between tertiary amines and simple ketones, and it proceeds by synergistic multiple catalysis with substoichiometric amounts of a hydrogen acceptor. This process is enabled by a simple chiral primary amine catalyst through the coupling of a catalytic enamine intermediate and an iminium cation intermediate in situ generated from tetrahydroisoquinoline derivatives by coupled Ru/Co catalysis.

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

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Intermolecular acetoxyaminoalkylation of alpha-diazo amides with (diacetoxyiodo)benzene and amines

Multicomponent reactions of diazo compounds have attracted much attention in recent years. Such transformations are generally conducted by applying transition metal catalysis and involve the corresponding metal carbenes as key intermediates. In this letter, a metal-free three-component intermolecular acetoxyaminoalkylation of alpha-diazo amides with tertiary aryl amines and (diacetoxyiodo)benzene is presented.

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

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Visible-Light-Mediated C(sp3)?H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)?H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.

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

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Solvent free amination reactions of aryl bromides at room temperature catalyzed by a (pi-allyl)palladium complex bearing a diphosphinidenecyclobutene ligand

An air- and moisture-stable (pi-allyl)palladium complex bearing a unique diphosphinidenecyclobutene ligand effectively catalyzes amination reactions of aryl bromides with amines, where the reactions proceed under mild conditions without solvent, with 2 mol % of catalyst and 1 equiv of t-BuOK at room temperature. Under these conditions the amination products were obtained in good to excellent isolated yields.

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

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N-Substituted Auxiliaries for Aerobic Dehydrogenation of Tetrahydro-isoquinoline: A Theory-Guided Photo-Catalytic Design

Visible-light mediated aerobic dehydrogenation of N-heterocyclic compounds is a reaction with enormous potential for application. Herein, we report the first complete aerobic dehydrogenation pathway to large-scale production of isoquinolines. The discovery of this visible light photoredox reaction was enabled through the combination of mathematical simulations and real-time quantitative mass spectrometry screening. The theoretical calculations showed that hyper-conjugation, the main underlying factor hindering the aerobic oxidation of tetrahydroisoquinolines, is relieved both by pi- and sigma-donating substituents. This mechanistic insight provided a novel photocatalytic route based on N-substituted auxiliaries that facilitated the conversion of tetrahydroisoquinolines into the corresponding isoquinolines in just three simple steps (yield 71.7% in bulk-solution phase), using unmodified Ru(bpy)3Cl2 photocatalyst, sun energy, atmospheric O2, and at ambient temperature.

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

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Covalent organic framework as an efficient, metal-free, heterogeneous photocatalyst for organic transformations under visible light

Visible-light active, heterogeneous, and organic photocatalysts exhibit a more sustainable and environmentally friendly alternative to classical metal-based catalysts. Two-dimensional covalent organic frameworks (2D-COFs) with permanent porosity, columnar pi-arrays and excellent stability, that can become an excellent platform for heterogeneous photocatalysis of organic transformations. Here we report a predesigned imine-based COF with electron donor and acceptor structure. And new framework possesses large surface area, high crystallinity, outstanding stability and broad absorption range in the visible-light region as well as good photoelectric response characteristics. Importantly, it was found to be a highly effective heterogeneous photocatalyst for reductive dehalogenation of phenacyl bromide derivatives and alpha-alkylation of aldehydes under irradiation of visible-light. In addition, the COF gave good recyclability and could be reused after a simple separation manipulation. The current present still reveals a great prospect for 2D-COFs as metal-free, heterogeneous photocatalysts for organic transformations.

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

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Cobalt-Catalyzed oxidative alpha-cyanation of tertiary aromatic amines with trimethylsilyl cyanide and tert -butyl hydroperoxide

In this Letter is described that a cobalt(II)-tert-butyl hydroperoxide oxidizing system was used to catalyze the alpha-cyanation of aromatic tertiary amines in the presence of trimethylsilyl cyanide to produce the corresponding alpha-aminonitriles in good yields. Georg Thieme Verlag Stuttgart. New York.

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

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CuBr-catalyzed oxidative difluoromethylation of tertiary amines with difluoroenol silyl ethers

CuBr-catalyzed oxidative difluoromethylation of readily available tertiary amines with difluoroenol silyl ethers was performed under mild conditions to afford beta-amine-a,a-difluoro ketones.

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

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The oxidative Mannich reaction catalyzed by dirhodium caprolactamate

Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction. The reaction proceeds via C-H oxidation of a tertiary amine followed by nucleophilic capture. This green transformation is conducted in protic solvent using inexpensive T-HYDRO (70% t-BuOOH in water). Synthetically valuable gamma-aminoalkyl butenolides are obtained. Copyright

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

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Selective cross-dehydrogenative coupling of N-phenyltetrahydroisoquinolines in aqueous media using poly(aniline sulfonic acid)/gold nanoparticles

Selective cross-dehydrogenative coupling of N-phenyltetrahydroisoquinoline with carbon nucleophiles such as dimethyl malonate, ethyl acetoacetate, and nitromethane was demonstrated in complete aqueous media using poly(2-methoxyaniline-5-sulfonic acid)/gold nanoparticles under molecular oxygen.

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