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Mechanistic Studies on Bioinspired Aerobic C-H Oxidation of Amines with an ortho-Quinone Catalyst

We report herein our mechanistic studies of the ortho-quinone-catalyzed aerobic oxidation of primary, secondary, and tertiary amines. Two different catalytic pathways were discovered for the reductive half reactions: for primary amines, the reaction was found to proceed via a transamination pathway, while the reactions with secondary amines and tertiary amines proceeded via hydride transfer. We also found that the amine substrates could significantly promote the regeneration of the ortho-quinone catalyst in the oxidative half reaction, in which a proton transfer occurs between the amine substrates and catechol derivatives (the reduced form of the ortho-quinone catalyst).

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

Extracurricular laboratory:new discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Sunflow: Sunlight Drives Fast and Green Photochemical Flow Reactions in Simple Microcapillary Reactors ? Application to Photoredox and H-Atom-Transfer Chemistry

?Sunflow? ? The combination of a microcapillary reactor in continuous flow mode with sunlight as the most sustainable energy source imaginable was applied to a range of photoredox and H-atom-transfer reactions making them both fast and green.

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

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Aerobic oxidative Mannich reaction promoted by catalytic amounts of stable radical cation salt

A catalytic amount of triarylaminium salt is demonstrated to be an efficient initiator for oxidative Mannich reaction of tertiary amines and nonactivated ketones under mild neutral conditions. Air is essential for this reaction and acts as a terminal oxidant. Metal catalysts, acid or base additives, and stoichiometric amounts of chemical oxidants are all avoided in this methodology. Six examples of intramolecular cyclized products are also delivered. (Chemical Equation Presented).

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

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The singlet excited state of BODIPY promoted aerobic cross-dehydrogenative-coupling reactions under visible light

In contrast to previous studies, we disclose for the first time that the singlet excited state (1PS?) of BODIPY rather than the triplet excited state (3PS?) can drive C-H bond activation to form C-C and C-P bonds smoothly, which offers new methods to promote organic transformation under visible light irradiation.

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

Extracurricular laboratory:new discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 3340-78-1 is helpful to your research. Synthetic Route of 3340-78-1

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Photoredox catalytic organic reactions promoted with broadband visible light-absorbing Bodipy-iodo-aza-Bodipy triad photocatalyst

The 4-bora-3a,4a-diaza-s-indacene scaffold is known as Bodipy. 2,6-Diiodo-aza-Bodipy (B-1) and the Bodipy-2,6-diiodo-aza-Bodipy triad (B-2) have been used as novel photocatalysts for photoredox catalytic organic reactions with tetrahydroisoquiniline as substrate to prepare highly functionalized organic compounds via a [3 + 2] cycloaddition-aromatization tandem reaction and Cu(i)-catalyzed alkynylation reactions. In distinction to conventional photocatalysts such as Ru(bpy)3Cl2, Eosin Y or Rose Bengal, which are based on a mono-visible light-harvesting chromophore profile and show weak absorption in the visible region, the new photocatalysts are strong visible absorbers (B-1, epsilon = 73000 M-1 cm-1 at 683 nm). More importantly, resonance energy transfer (RET) has been used to increase the absorption of photocatalyst B-2 in the visible region, in which two Bodipy units were used as energy donor and diiodo-aza-Bodipy as energy acceptor. B-2 shows broadband absorption in the range 400-750 nm (epsilon = 165 000 M-1 cm-1 at 504 nm, and 71000 M-1 cm -1 at 683 nm). Iodo-aza-Bodipy is more efficient than conventional photocatalysts such as [Ru(bpy)3]Cl2. Furthermore, the broadband visible light-absorbing B-2 is more efficient as a photocatalyst than previously reported monochromophore photocatalyst B-4 (diiodo-Bodipy). Our results will be useful for the design of efficient organic triplet photosensitizers as photocatalysts for photoredox catalytic organic reactions. This journal is the Partner Organisations 2014.

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

Extracurricular laboratory:new discovery of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Visible-light-induced direct alpha-C(sp3)-H thiocyanation of tertiary amines

Visible-light-induced, eosin Y catalyzed aerobic oxidative alpha-C(sp3)-H thiocyanation of tertiary amines is reported. The reaction proceeds through visible-light-induced in situ generation of the iminium ion followed by attack of -SCN nucleophile. This is the first example of visible-light-initiated formation of C(sp3)-S bond employing organo-photoredox catalysis. Mild reaction conditions and use of air and visible light as the greenest and sustainable reagents at room temperature are the salient features of the protocol.

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

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

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Direct sp3 C-H acroleination of N-aryl-tetrahydroisoquinolines by merging photoredox catalysis with nucleophilic catalysis

Sequence catalysis merging photoredox catalysis (PC) and nucleophilic catalysis (NC) has been realized for the direct sp3 C-H acroleination of N-aryl-tetrahydroisoquinoline (THIQ). The reaction was performed under very mild conditions and afforded products in 50-91% yields. A catalytic asymmetric variant was proved to be successful with moderate enantioselectivities (up to 83 : 17 er).

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

Discovery of 3340-78-1

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Chemotherapeutic agents

A method of treating or preventing viral infections, in particular rhinovirus infections comprising the administration of an effective amount of a 2-phenyltetralin derivative or a heterocyclic analogue thereof. Pharmaceutical compositions containing these compounds, and some novel compounds are also disclosed.

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

Brief introduction of 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights

A family of quinoline-platinum(II) complexes as efficient photocatalysts is presented. Their key characteristic is their easy preparation by coordination of the readily available 8-hydroxy- or 8-thio-quinoline ligands, which are well known for their strong chelating ability to different metal ions. In the different photochemical transformations investigated, such as cross-dehydrogenative coupling, oxidation of arylboronic acids, and asymmetric alkylation of aldehydes, 8-mercaptoquinoline-Pt(II) complex proved to be the most general catalyst. Moreover, quenching experiments showed that, contrary to related methods reported in the literature, these complexes followed an oxidative quenching mechanism in all transformations studied. Besides, simulations performed with high-level ab initio methods of the complexes have helped to understand their photocatalytic activity.

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

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Mixed-Ligand Metal-Organic Framework for Two-Photon Responsive Photocatalytic C-N and C-C Coupling Reactions

A multiple-photon photochemical process breaks the existing energy limitation of visible-light photocatalysis. Through careful incorporation of both bis(3,5-dicarboxyphenyl)pyridine and bis(3,5-dicarboxyphenyl)methylpyridinium ligands into a single metal-organic framework (MOF), we report herein photocatalytic C-N and C-C oxidative coupling reactions that evidenced the direct two-photon response process. Time-dependent luminescence-decay studies demonstrated that the framework reached the same excited state by a two-photon absorption process as that reached via a single-photon absorption process, and the excited state could activate substrates even under NIR-light irradiation. Under 660 nm light-emitting diode (LED) irradiation, both the photooxidative C-N coupling reaction of benzylamine to form benzylidene-1-phenylmethanamine and the C-C coupling reaction between nitromethane and N-phenyltetrahydroisoquinoline were accelerated directly in a heterogeneous manner. Control experiments suggested that minimal byproducts were formed under the NIR-light irradiation compared to those of the UV light catalytic reactions. Importantly, photon intensity-dependent studies exhibited a nonlinear correlation between catalytic efficiency of multivariate MOFs (MTV-MOFs) and photon power intensity, verifying the two-photon responsive nature, which indicated that metal-organic framework with high density and ordered photoactive motifs could enhance the two-photon absorption ability, thereby improving photocatalytic efficiency even under LED irradiation.

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