Awesome Chemistry Experiments For 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Visible-light photoredox catalysis: Aza-Henry reactions via C-H functionalization

(Chemical Equation Presented) We report the application of visible-light photoredox catalysis for the formation of C-C bonds between tertiary N-arylamines and nitroalkanes via an oxidative aza-Henry reaction. In the presence of 1 mol % Ir(ppy)2(dtbbpy)PF6, efficient coupling of nitroalkanes with in situ-generated iminium ions provides the desired products in up to 96% yield. Mechanistic studies suggest that reductive quenching of the Ir3+ excited state by the tertiary amine leads to the ammonium radical cation, with subsequent catalyst turnover (Ir2+ ? Ir3+) likely effected by atmospheric oxygen. Copyright

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

Top Picks: new discover of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Engineering coordination polymers for photocatalysis

Photocatalysis has been distinguished itself as one of the most promising technologies from the wide variety of renewable energy projects underway, as it represents a promising approach to realize solar energy conversion. Under light irradiation, semiconductors (TiO2, Ag3PO4, WO3, CdS, and ZnS etc.) have demonstrated great potential in photolysis of water to yield hydrogen fuel, decomposition or oxidization of hazardous substances, photoelectrochemical conversion, as well as artificial photosynthesis. However, the disadvantages of easy agglomeration, and low solar energy conversion efficiency of these inorganic catalysts limit their large scale applications. Developing new photocatalysts has been attracting great attention in the related research communities. Owing to their structural diversity and controllable synthetic procedures, coordination polymers (CPs) provide a newly emerging platform to organize light-harvesting antennae and catalytic centers to achieve solar energy conversion. Besides, controllable integration of CPs with functional materials is leading to the creation of new multifunctional composites/hybrids, which exhibit superior photocatalytic performances to those of the individual components due to the collective behavior of the functional units. In this article, the latest advances of CPs based materials in the application of photocatalysis are critically reviewed, and the main approaches for efficient light harvesting and active site engineering in CPs-based photocatalysts are discussed. The main advantages of CPs as photocatalysts and the challenges faced for further improving catalytic performance are also highlighted.

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

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Anionic Cyclometalated Platinum(II) Tetrazolato Complexes as Viable Photoredox Catalysts

The synthesis, characterization, photophysical and photocatalytic studies of anionic platinum(II) tetrazolato complexes, with the general structure [TBA][Pt(CNC)TzR], are reported, where CNC2- represents a doubly cyclometalated 2,4,6-triphenylpyridine, TzR- is an anionic 5-substituted tetrazolato ligand (with a variable R functional group), and TBA+ is the tetrabutylammonium countercation. The complexes were prepared by substitution of the DMSO ligand in [Pt(CNC)(DMSO)] with the corresponding tetrazolato ligand. No emission from the platinum(II) complexes was detected at room temperature in solution, but the photophysical properties could be assessed in the solid state, where all the complexes display emission bands attributed to aggregates. The platinum(II) complexes were found to facilitate a range of fundamental classes of visible-light-mediated photoredox-catalyzed reactions, including alpha-amino C-H functionalization processes, such as Povarov-type reactions and the addition of alpha-amino C-H bonds across Michael acceptors, in addition to ATRA chemistry, and a hydrodeiodination. With the exception of the hydrodeiodination process, the best Pt(II) catalysts provided turnover numbers of 150-175 in each of these transformations.

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

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Visible-Light-Driven Decarboxylative Alkylation of C-H Bond Catalyzed by Dye-Sensitized Semiconductor

A decarboxylative alkylation of benzylic C(sp3)-H bonds of N-aryl tetrahydroisoquinolines under the irradiation of blue light is reported, featuring a broad substrate scope, low cost, heavy-metal-free, and mild conditions. A preliminary mechanistic study indicated that radical intermediates are involved during the course of the reaction.

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

The important role of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Iminium Ion and N-Hydroxyimide as the Surrogate Components in DEAD-Promoted Oxidative Ugi Variant

A practical metal-free oxidative Ugi-type three-component assembly has been achieved efficiently, employing a tertiary-amine-derived iminium ion as an imine surrogate, N-hydroxyimide as an acid surrogate, and DEAD as an oxidant. This dual-surrogate Ugi variant proceeded with a broad substrate scope and desired functional group tolerance, leading to a wide range of N-alkyl-N-acyl aminophthalimide and N-alkyl-N-acylaminosuccinimide derivatives in good isolated yields.

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

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Magnetic nanoparticle-supported eosin Y ammonium salt: An efficient heterogeneous catalyst for visible light oxidative C?C and C?P bond formation

A highly efficient visible light mediated C?C and C?P coupling reactions of sp3 C?H bonds adjacent to the nitrogen atom in tetrahydroisoquinoline derivatives with pronucleophiles such as nitroalkanes, malononitrile, dimethyl malonate and H-phosphonate diesters were achieved by using a magnetic nanoparticle-supported eosin Y bis-benzyltriethylammonium salt (MNPs-Eosin Y) as catalyst and air as the sole oxidant, affording the corresponding products in good to excellent yields under mild reaction conditions. Notably, the supported eosin Y catalyst can easily be separated from the reaction mixture by an external permanent magnet and can be recycled at least eight times without a significant loss of activity.

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

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Graphite-supported gold nanoparticles as efficient catalyst for aerobic oxidation of benzylic amines to imines and N-substituted 1,2,3,4- tetrahydroisoquinolines to amides: Synthetic applications and mechanistic study

Selective oxidation of amines using oxygen as terminal oxidant is an important area in green chemistry. In this work, we describe the use of graphite-supported gold nanoparticles (AuNPs/C) to catalyze aerobic oxidation of cyclic and acyclic benzylic amines to the corresponding imines with moderate-to-excellent substrate conversions (43-100%) and product yields (66-99%) (19 examples). Oxidation of N-substituted 1,2,3,4- tetrahydroisoquinolines in the presence of aqueous NaHCO3 solution gave the corresponding amides in good yields (83-93%) with high selectivity (up to amide/enamide=93:4) (6 examples). The same protocol can be applied to the synthesis of benzimidazoles from the reaction of o-phenylenediamines with benzaldehydes under aerobic conditions (8 examples). By simple centrifugation, AuNPs/C can be recovered and reused for ten consecutive runs for the oxidation of dibenzylamine to N-benzylidene(phenyl) methanamine without significant loss of catalytic activity and selectivity. This protocol “AuNPs/C+O 2” can be scaled to the gram scale, and 8.9 g (84% isolated yield) of 3,4-dihydroisoquinoline can be obtained from the oxidation of 10 g 1,2,3,4-tetrahydroisoquinoline in a onepot reaction. Based on the results of kinetic studies, radical traps experiment, and Hammett plot, a mechanism involving the hydrogen-transfer reaction from amine to metal and oxidation of M-H is proposed.

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

Awesome Chemistry Experiments For 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3

A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.

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

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Porous chitosan microspheres supported-palladium catalyst for the C-N cross-coupling of aryl halides with secondary amines

Porous chitosan microspheres-supported palladium catalysed the amination of aryl halides with a wide variety of secondary amines to yield the corresponding cross-coupling products under aerobic conditions. Both aryl bromides and iodides gave good to excellent yields of N,N-disubstituted anilines. The procedure can tolerate common functional groups such as chloro, methoxyl and nitro. The heterogeneous catalysis is efficienct and the catalyst could be recycled seven times without obvious decreased conversion.

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

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Phosphoryl chloride-mediated solvent-free synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers

A solvent- and metal-free protocol for preparation of N-aryl substituted azacycles from arylamines and cyclic ethers is described. In this method, the combination of POCl3 and DBU is crucial for conversion of arylamines and cyclic ethers to five- and six-membered azacycles. Without solvent, a variety of N-aryl-substituted, five-membered azacycles (pyrrolidines, 2-methylpyrrolidines, and piperidine) and six-membered azacycles (isoindolines and tetrahydroisoquinolines) are synthesized in high yields. This green method provides a sustainable and efficient approach for the preparation of azacycles from various cyclic ethers.

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