Discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Oxidative Cyclization Synthesis of Tetrahydroquinolines and Reductive Hydrogenation of Maleimides under Redox-Neutral Conditions

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

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

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New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines

Thiourea itself has been introduced as a mild and efficient organocatalyst for the oxidative alpha -cyanation of N-aryltetrahydroisoquinolines (THIQs) with trimethylsilyl cyanide (TMSCN), giving the corresponding products in good to excellent yields. Experimental investigations demonstrated that thiourea acts as a radical initiator by abstracting hydroxyl radical ([rad]OH) from tert-butyl hydroperoxide (TBHP) directly instead of non-covalent hydrogen bondings (H-bondings) activation. The use of thiourea as a radical initiator offers a new avenue for innovative chemical transformations in organocatalyzed radical chemistry.

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

New explortion of 3340-78-1

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Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates

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

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

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A robust palladium(II)-Porphyrin complex as catalyst for visible light induced oxidative C-H functionalization

A series of palladium(II)-porphyrin complexes that display dual emissions with lifetimes up to 437mus have been synthesized. Among the four complexes, PdF20TPP is an efficient and robust catalyst for photoinduced oxidative C-H functionalization by using oxygen as terminal oxidant. alpha-Functionalized tertiary amines were obtained in good to excellent yields by light irradiation (lambda>400nm) of a mixture of PdF20TPP, tertiary amine, and nucleophile (cyanide, nitromethane, dimethyl malonate, diethyl phosphite, and acetone) under aerobic conditions. Four examples of intramolecular cyclized amine compounds could be similarly prepared. Comparison of the UV-visible absorption spectra before and after the photochemical reaction revealed that PdF20TPP was highly robust (>95 % recovery). The practical application of PdF20TPP has been revealed by the photochemical reactions performed by using a low catalyst loading (0.01mol %) and on a 10mmol scale. The PdF20TPP catalyst could sensitize photoinduced oxidation of sulfides to sulfoxides in excellent yields. Mechanistic studies revealed that the photocatalysis proceeded by singlet-oxygen oxidation. Long-lived excited states! A series of palladium(II)-porphyrin complexes have been synthesized and found to display long-lived excited states with lifetimes up to 437mus (see scheme). Among these complexes, PdF 20TPP is an efficient and robust catalyst for a broad array of photoinduced oxidative C-H functionalization reactions. PtF20TPP= platinum(II) meso-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin.

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

Simple exploration of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Metal-free photocatalysts for the oxidation of non-activated alcohols and the oxygenation of tertiary amines performed in air or oxygen

This protocol describes the use of 9-fluorenone as a cheap and non-toxic photocatalyst for the oxidation of non-activated alcohols performed under the irradiation of a blue light-emitting diode. It also describes the use of the similarly cheap and non-toxic photocatalyst rose bengal for the selective alpha-oxygenation of tertiary amines to produce the corresponding amides in a selective way using the same light source. We have provided detailed instructions on how to assemble the light-emitting diode equipment and set up the photocatalytic reaction, where an oxygen atmosphere is created with an O2-filled balloon. Further details are provided using four example reactions that illustrate how this system works: alcohol oxidation to prepare terephthlalaldehyde and androstanedione, and amine oxidation to make 2-phenyl-3,4-dihydroisoquinolin-1(2H)-one and (4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)m-tolyl)methanone. The times needed to perform these photocatalytic reactions are 18, 76, 22 and 54 h, respectively. We believe that this protocol represents a robust methodology for the late-stage modification of amines and the selective oxidation of steroids.

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

A new application about 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Highly efficient visible-light-induced aerobic oxidative C-C, C-P coupling from C-H bonds catalyzed by a gold(III)-complex

A novel and highly efficient gold(III)-complex catalyzed aerobic oxidative alpha-C-H functionalization of amines has been developed. The tertiary amines can be directly coupled with various nucleophiles using air as a sustainable oxidant.

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

Final Thoughts on Chemistry for 3340-78-1

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Synthesis of Dihydroindoloisoquinolines through Copper-Catalyzed Cross-Dehydrogenative Coupling of Tetrahydroisoquinolines and Nitroalkanes

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

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Acetone cyanohydrin: A convenient alternative of toxic sodium cyanide/acetic acid for oxidative cyanation of tertiary amines

Acetone cyanohydrin was found to be a facile, convenient and comparatively safer alternative to toxic sodium cyanide/acetic acid system for generating in situ HCN for the oxidative cyanation of tertiary amines to alpha-aminonitriles in high yields with hydrogen peroxide using RuCl3 as catalyst. In addition organic nature of acetone cyanohydrin makes it more suitable for an organic transformation since it is readily soluble in reaction medium and can be added in a controlled manner. Graphical Abstract: [Figure not available: see fulltext.]

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

Extended knowledge of 3340-78-1

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Polydimethylsiloxane Sponge-Supported Nanometer Gold: Highly Efficient Recyclable Catalyst for Cross-Dehydrogenative Coupling in Water

Polydimethylsiloxane (PDMS, a stable hydrophobic polymer material) sponge-supported nanometer-sized gold can be used as a highly efficient recyclable catalyst for cross-dehydrogenative coupling of tertiary amines with various nucleophiles in water. This PDMS sponge nanometer gold catalyst can provide much better activity than the free nanometer gold in water. The reaction can be scaled up by using an easy-to-build continuous flow reactor. These results indicate the potential application of porous hydrophobic PDMS sponge material as a promising support for highly efficient recyclable catalysts in water.

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

Archives for Chemistry Experiments of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Oxidative Difluoromethylation of Tetrahydroisoquinolines Using TMSCF2SPh: Synthesis of Fluorinated Pyrrolo[2,1-a]isoquinolines and Benzo[a]quinolizidines

An efficient C1-difluoromethylation of tetrahydroisoquinolenes was achieved using TMSCF2SPh as a difluoromethylating agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO+BF4-) as an oxidant. The process provides an access to a variety of C1-difluoro(phenylsulfanyl)methylated tetrahydroisoquinoline adducts in good yields. These adducts were employed as key precursors for preparing fluorinated pyrrolo[2,1-a]isoquinoline and benzo[a]quinolizidines.

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