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DEAD-Promoted Oxidative Ugi-Type Reaction Including an Unprecedented Ugi Amidation Assisted by Dicarboxylic Acids

A mild and metal-free DEAD-promoted (DEAD = diethyl azodicarboxylate) oxidative Ugi-type reaction of tertiary amines has been demonstrated. The reaction gives easy access to alpha-amino amides and imides with diverse functional groups in good isolated yields. This Ugi-type approach achieves an unprecedented synthesis of alpha-amino amide analogues with the assistance of dicarboxylic acids, and not water, for the introduction of the carbonyl oxygen atom of the amide moiety. Mechanistic studies indicated that the dicarboxylic acids may readily undergo an intramolecular annulation, instead of the Mumm rearrangement, to give the desired amide with one molecule of anhydride released.

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

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Cobalt(II)-catalyzed oxidative coupling of aromatic tertiary amines with enol silyl ethers leading to beta-aminoketone derivatives

We demonstrated that a cobalt(II)-TBHP (tert-butyl hydroperoxide) oxidizing system efficiently catalyzes the coupling of aromatic tertiary amines with enol silyl ethers, producing the corresponding beta-aminoketones.

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

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Luminescent palladium(II) complexes with pi-extended cyclometalated [R-C^N^N-R?] and pentafluorophenylacetylide ligands: Spectroscopic, photophysical, and photochemical properties

A series of cyclometalated PdII complexes that contain pi-extended R-C^N^N-R? (R-C^N^N-R?=3-(6?-aryl-2?- pyridinyl)isoquinoline) and chloride/pentafluorophenylacetylide ligands have been synthesized and their photophysical and photochemical properties examined. The complexes with the chloride ligand are emissive only in the solid state and in glassy solutions at 77 K, whereas the ones with the pentafluorophenylacetylide ligand show phosphorescence in the solid state (lambdamax=584-632 nm) and in solution (lambdamax=533- 602 nm) at room temperature. Some of the complexes with the pentafluorophenylacetylide ligand show emission with lambdamax at 585-602 nm upon an increase in the complex concentration in solutions. These PdII complexes can act as photosensitizers for the light-induced aerobic oxidation of amines. In the presence of 0.1 mol % PdII complex, secondary amines can be oxidized to the corresponding imines with substrate conversions and product yields up to 100 and 99 %, respectively. In the presence of 0.15 mol % PdII complex, the oxidative cyanation of tertiary amines could be performed with product yields up to 91 %. The Pd II complexes have also been used to sensitize photochemical hydrogen production with a three-component system that comprises the PdII complex, [Co(dmgH)2(py)Cl] (dmgH=dimethylglyoxime; py=pyridine), and triethanolamine, and a maximum turnover of hydrogen production of 175 in 4 h was achieved. The excited-state electron-transfer properties of the PdII complexes have been examined. Copyright

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

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A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations

A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this “green” methodology was further demonstrated by applying in bioactive and drug valued target syntheses.

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

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Dual copper- and photoredox-catalysed reactions

The merger of transition metal catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile way of developing new synthetic methodologies. This review will focus on the relatively new but fast expanding area of dual copper- and photoredox-catalysis, detailing recent developments in the area.

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

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3340-78-1, Name is 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, belongs to tetrahydroisoquinoline compound, is a common compound. Application In Synthesis of 2-Phenyl-1,2,3,4-tetrahydroisoquinolineIn an article, once mentioned the new application about 3340-78-1.

Reactions Catalysed by a Binuclear Copper Complex: Relay Aerobic Oxidation of N-Aryl Tetrahydroisoquinolines to Dihydroisoquinolones with a Vitamin B1 Analogue

N-Aryl tetrahydroisoquinolines were oxidised to dihydroisoquinolones through the relay catalysis of a binuclear paddle-wheel copper complex and a vitamin B1 analogue with oxygen as oxidant. Mechanistic studies revealed that the copper catalyst oxidises amines to the corresponding iminium salts, which are then oxygenated to lactam products by catalysis of the vitamin B1 analogue.

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

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Synthesis and reactivity of pentavalent biphenyl-2,2?-ylenebismuth derivatives

Phenylbiphenyl-2,2?-ylenebismuth diacetate reacted with nucleophiles under basic conditions to give modest to good yields of the C-phenylated substrates. Under copper catalysis, it reacted with hydroxy or amino groups to give the products of O- or N-phenylation. In both sets of reaction conditions, this reagent showed a reduced reactivity compared to the analogous triphenylbismuth diacetate reagent. It showed also a high regioselectivity as only the phenyl derivatives were detected and isolated. The Royal Society of Chemistry 2000.

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

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A ruthenium-carbamato-complex derived from a siloxylated amine and carbon dioxide for the oxidative alpha-cyanation of aromatic and cyclic tertiary amines

The ruthenium carbamate complex derived from 3-trimethoxysilyl-1-propyl amine and carbon dioxide was found to be a novel catalyst for the oxidative cyanation of aromatic and cyclic tertiary amines to corresponding alpha-amino nitriles in high to excellent yields by using hydrogen peroxide and molecular oxygen as enviro-economic oxidants. The developed protocol suggested an efficient alternative for recycling carbon dioxide.

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

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Regiodivergent Hydroaminoalkylation of Alkynes and Allenes by a Combined Rhodium and Photoredox Catalytic System

A rhodium/photoredox dual catalyzed regiodivergent alpha-allylation of amines is described. As an atom-economic and efficient method, alkynes and allenes are used as allylic electrophile surrogates in this novel protocol. With different reaction conditions, synthetically useful branched or linear homoallylic amines could be synthesized in good to excellent yields and regioselectivity. This straightforward strategy complements the traditional transition-metal catalyzed allylation reactions.

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

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Catalytic asymmetric activation of a Csp3-H bond adjacent to a nitrogen atom: A versatile approach to optically active alpha-alkyl alpha-amino acids and C1-alkylated tetrahydroisoquinoline derivatives

Simple and efficient: A one-pot oxidative and catalytic enantioselective alkylation of alpha-C sp 3-H bonds adjacent to a nitrogen atom was realized for the first time. This novel strategy provides a simple, efficient, and environmentally friendly access to diverse optically active alpha-alkyl alpha-amino acid and C1-alkylated tetrahydroisoquinoline derivatives. Copyright

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