Category: 3340-78-1

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A novel method for the synthesis of alpha-aminonitrile through visible-light-induced oxidative cyanation of N-aryltetrahydroisoquinoline with potassium thiocyanate has been developed. The process does not require the use of a photocatalyst, transition metal reagent, strong oxidizing agent, or toxic cyano-containing compound, which makes the reaction simple and green.

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

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An efficient visible-light-induced alpha-oxidation of N-substituted tetrahydroisoquinolines to dihydroisoquinolones has been developed using eosin Y as an organo-photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones were obtained in up to 96% yield at room temperature under oxygen atmosphere. This transformation provides a convenient route to dihydroisoquinolones with a wide range of substrates. (Figure presented.).

The π-electrons of these planar compounds are free to cycle around the circular arrangements of atoms found in the aromatic moieties. This stems from the resonance found in planar ring systems, like benzene, and 3340-78-1

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

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. An article , which mentions Reference of 3340-78-1, molecular formula is C15H15N. The compound – 2-Phenyl-1,2,3,4-tetrahydroisoquinoline played an important role in people’s production and life., Reference of 3340-78-1

The direct formation of new C-C bonds through photocatalytic oxidative coupling from low reactive sp3 C-H bonds using environmentally benign and cheap oxygen as oxidant is an important area in sustainable chemistry. By incorporating the photoredox catalyst [SiW11O39Ru(H2O)]5- into the pores of Cu-based metal-organic frameworks, a new approach for merging Cu-catalysis/Ru-photocatalysis within one single MOF was achieved. The direct CuII-O-W(Ru) bridges made the two metal catalyses being synergetic, enabling the application on the catalysis of the oxidative coupling C-C bond formation from acetophenones and N-phenyl-tetrahydroisoquinoline with excellent conversion and size-selectivity. The method takes advantage of visible light photoredox catalysis to generate iminium ion intermediate from N-phenyl-tetrahydroisoquinoline under mild conditions and the easy combination with Cu-catalyzed activation of nucleophiles. Control catalytic experiments using similar Cu-based sheets but with the photoredox catalytic anions embedded was also investigated for comparison.

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

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The question of whether hydrogen atom transfer (HAT) or electron transfer (ET) is the key step in the activation of N-aryl tetrahydroisoquinolines in oxidative coupling reactions using CuBr as catalyst and tert-butyl hydroperoxide (tBuOOH) has been investigated. Strong indications for a HAT mechanism were derived by using different para-substituted N-aryl tetrahydroisoquinolines, showing that electronic effects play a minor role in the reaction. Hammett plots of the Cu-catalyzed reaction, a direct time-resolved kinetic study with in situ generated cumyloxyl radicals, as well as density functional calculations gave essentially the same results. We conclude from these results and from kinetic isotope effect experiments that HAT is mostly mediated by tert-butoxyl radicals and only to a lesser extent by tert-butylperoxyl radicals, in contrast to common assumptions. However, reaction conditions affect the competition between these two pathways, which can significantly change the magnitude of kinetic isotope effects.

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

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Construction of porous organic polymers (POPs) as metal-free heterogeneous organic photocatalysts for highly efficient catalytic organic transformations using visible light remains a key challenge. Herein, we report the ?bottom-up? strategy to facilely synthesize two Eosin Y dye-based POP frameworks (EY-POPs) for highly efficient heterogeneous organic-photocatalysis. Owing to the high BET surface area and the built-in character of the covalently linked catalytic sites of EY-POPs, these photoactive polymers show excellent catalytic activity in photocatalyzing the aza-Henry reaction. The superior utility of the EY-POP-1 polymer in catalysis was demonstrated by the broad scope of the reactants and the high yield of the reaction products. Moreover, the EY-POP-1 polymer shows robust recycling capability with good retention of photoactivity over at least twelve cycles without any significant loss of the catalytic activity (94-98% yield).

A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 3340-78-1

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

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A novel bifunctional organic sponge photocatalyst can enable the efficient coupling of tertiary amines with ketones in water. The asymmetric transformation can be also achieved by using this sponge photocatalyst.

Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.Formula: C15H15N, you can also check out more blogs about3340-78-1

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

The flat faces of aromatic rings also have partial negative charges due to the π-electrons. Similar to other non-covalent interactions –including hydrogen bonds, electrostatic interactions and Van der Waals interactions. Application of 3340-78-1, 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 breath of fresh air: The title reaction has been developed for the coupling of amines with nitroalkanes and different unmodified ketones using air as the sole oxidant under mild reaction conditions. The safe, convenient, and environmentally benign process, as well as the low catalyst loading, short reaction time, and good yields make this protocol very practical (see scheme). Copyright

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

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We have exploited a bis(1,10-phenanthroline)copper(I) visible light photocatalyst (VLP), [Cu(dap)2]+, to effect the direct alpha-C-H functionalization of amines. To our knowledge, this represents the first example of the oxidation of amines that are ultimately incorporated into synthetic targets by a copper(I) VLP. We have utilized this approach to rapidly prepare unprecedented octahydroisoquinolino[2,1-a]pyrrolo[3,4-c]quinoline frameworks and exploited this process to synthesize a novel aglycone analogue of the natural product incargranine B. Most significantly, our studies suggest that the presence of trifluoroacetic acid (TFA) is crucial in mediating the aerobic oxidative quenching of a putative photoexcited copper(I) species involved in the catalytic cycle.

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

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A copper/Bronsted acid dual-catalyst promoted oxidative cross-dehydrogenative-coupling of alkylazaarenes and tertiary amines for C(sp3)-C(sp3) bond formation was developed. This method uses dioxygen as the terminal oxidant under mild reaction conditions and would provide a convenient benzylic C-H transformation of alkylazaarenes to biologically active pharmaceutics. the Partner Organisations 2014.

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

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The various alpha-aminophosphonates have been prepared from tertiary aromatic and aliphatic amines with P(O)H compounds via a tert -butyl hydroperoxide mediated cross-dehydrogenative coupling reaction, eliminating the need for transition-metal catalysts. The oxidation of tertiary amine by tert -butyl hydroperoxide generates an iminium cation intermediate. A further addition of P(O)H compound to iminium cation gives the desired product.

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