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

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Importance of Singlet Oxygen in Photocatalytic Reactions of 2-Aryl-1,2,3,4-tetrahydroisoquinolines Using Chalcogenorosamine Photocatalysts

Aerobic oxidation of 2-aryl-1,2,3,4-tetrahydroisoquinolines was achieved photocatalytically using chalcogenorosamine photocatalysts and LED irradiation. The photocatalytic aza-Henry reaction between these substrates and nitromethane was more efficient with selenorosamine and tellurorosamine photocatalysts than with thiorosamine and rosamine photocatalysts, corresponding to the propensity of the photocatalysts to generate singlet oxygen (1O2). Appropriately, yields for the photocatalytic aza-Henry reaction were greatly reduced when the reactions were conducted under a nitrogen atmosphere. The 2-aryl-1,2,3,4-tetrahydroisoquinolines were oxidized to the corresponding 2-aryl-3,4-dihydroisoquinolones 13a-13c with selenorosamine and tellurorosamine photocatalysts in 2% aqueous acetonitrile. Di-2-aryl-1,2,3,4-tetrahydroisoquinolin-1-yl peroxides 14a and 14b were shown to be intermediates in this reaction. Thiorosamine photocatalysts, which do generate 1O2 upon irradiation, did not give 2-aryl-3,4-dihydroisoquinolones. These results suggested that the exciplex between 1O2 and the chalcogen atom of the chalcogenorosamines (the corresponding pertelluoxide, perselenoxide, or persulfoxide) and/or the hydrated perchalcogenoxide [hydroxy (perhydroxy)tellurane, -selenane, or -thiane] might be an active oxidant in the formation of 13a-13c. Computational methods were employed to provide support for the observed photocatalytic reactivity of the tellurorhodamine and selenorhodamine chromophores compared to the thiorosamine chromophores. deltaG values were determined for the oxidation and hydration of 10-Te, 10-Se, and 10-S for formation of perchalcogenoxides and hydroxyl(perhydroxy)chalcogenanes, respectively. Calculations indicate formation of the pertelluroxide perselenoxide, and persulfoxide exciplex intermediates are energetically favorable. Hydration of the exciplexes of 10-Te and 10-Se have similarly small deltaG of -3.49 and 4.51 kcal/mol, respectively. However, a significantly higher deltaG value of +22.4 kcal/mol is observed for the hydration of 10-S, which suggests that this reactive intermediate is not readily formed.

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

Archives for Chemistry Experiments of 3340-78-1

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Synthetic Route of 3340-78-1, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 3340-78-1, molcular formula is C15H15N, introducing its new discovery.

Enantioselective cross dehydrogenative coupling reaction catalyzed by Rose Bengal incorporated-Cu(I)-dimeric chiral complexes

A novel dimeric chiral Cu(I) amino alcohol based in-situ generated catalyst in combination with Rose Bengal as a photo-redox catalyst were used for the first time for asymmetric cross dehydrogenative coupling of N-aryl tetrahydroisoquinoline with terminal alkynes enroute for propargylic amines synthesis using molecular oxygen as a terminal oxidant. This methodology provides an atom economical and green way to access diversified optically active alkynylation product selectively at C1-position of N-aryl tetrahydroisoquinoline under moderate conditions with high enantioselectivity (up to 99%) and excellent yield (up to 90%).

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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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Dehydrogenative C(sp3)-H bond functionalization of tetrahydroisoquinolines mediated by organic oxidants under mild conditions

The organocatalyzed Mannich reaction of unsubstituted and N-aryl-substituted tetrahydroisoquinolines (THIQs) and the Strecker reaction of several N-aryl-substituted THIQs through dehydrogenative C(sp3)-H bond functionalization (cross-dehydrogenative coupling) promoted by organic single electron oxidants DDQ and IBX are presented. The C-H oxidation/Mannich reaction of less reactive N-aryl substituted pyrrolidines is achieved via metal catalyzed photoredox catalysis. Operationally simple procedures provide desired products in an effective and time preserving manner.

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

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Direct and Efficient C(sp3)-H Bond Alkylation of Tetrahydroisoquinolines and Isochroman with Alkylzinc Reagents

An efficient C(sp3)?H bond alkylation of tetrahydroisoquinolines and isochroman with alkylzinc reagents was demonstrated. This transformation could be readily performed under mild conditions in the absence of a heavy metal catalyst, affording a wide range of potentially biologically active compounds. In addition, this approach exhibited excellent compatibility with various sensitive functional groups such as a cyano group, an ester group as well as a boronic acid pinacol ester group. (Figure presented.).

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

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A deprotection strategy of a BODIPY conjugated porous polymer to obtain a heterogeneous (dipyrrin)(bipyridine)ruthenium(II) visible light photocatalyst

This work shows that a deprotection strategy of BODIPY conjugated porous polymers (CMPBDPs) can be successfully applied to synthesize a new (dipyrrin)(bipyridine)Ru(ii) (CMPBDP-Ru) efficient heterogeneous photocatalyst for iminium ion generation under visible light. CMPBDP-Ru shows high thermal and photochemical stability under irradiation, and it could be reused several times.

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

A new application about 3340-78-1

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Uncatalyzed Oxidative C?H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study

A new method for the one-step C?H amination of xanthene and thioxanthene with sulfonamides is reported, without the need for any metal catalyst. A benzoquinone was employed as a hydride (or two-electron and one-proton) acceptor. Moreover, a previously unknown and uncatalyzed reaction between iminoiodanes and xanthene, thioxanthene and dihydroacridines (9,10-dihydro-9-heteroanthracenes or dihydroheteroanthracenes) is disclosed. The reactions proceed through hydride transfer from the heteroarene substrate to the iminoiodane or benzoquinone, followed by conjugate addition of the sulfonamide to the oxidized heteroaromatic compounds. These findings may have important mechanistic implications for metal-catalyzed C?H amination processes involving nitrene transfer from iminoiodanes to dihydroheteroanthracenes. Due to the weak C?H bond, xanthene is an often-employed substrate in mechanistic studies of C?H amination reactions, which are generally proposed to proceed via metal-catalyzed nitrene insertion, especially for reactions involving nitrene or imido complexes that are less reactive (i.e., less strongly oxidizing). However, these substrates clearly undergo non-catalyzed (proton-coupled) redox coupling with amines, thus providing alternative pathways to the widely assumed metal-catalyzed pathways.

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

More research is needed about 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Autoxidative carbon-carbon bond formation from carbonhydrogen bonds

(Figure Presented) Only oxygen and acid! The oxidative coupling of xanthene and other activated benzylic compounds with carbon nucleophiles such as ketones, can be performed under ambient conditions without solvent by simply using oxygen and catalytic amounts of methanesulfonic acid. The proposed reaction mechanism involves substrate activation by formation of hydroperoxides; the method can therefore be regarded as an “autoxidative coupling reaction”.

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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.

Aerobic and electrochemical oxidative cross-dehydrogenative-coupling (CDC) reaction in an imidazolium-based ionic liquid

The ionic liquid 1-butyl-3methylimidazolium tetrafluoroborate [BMIm][BF4] has demonstrated high efficiency when applied as a solvent in the oxidative nitro-Mannich carboncarbon bond formation. The coppercatalyzed cross-dehydrogenative coupling (CDC) between N-phenyltetrahydroisoquinoline and nitromethane in [BMIm][BF4] occurred with high yield under the described reaction conditions. Both the ionic liquid and copper catalyst were recycled nine times with almost no lost of activity. The electrochemical behavior of the tertiary amine substrate and beta-nitroamine product was investigated employing [BMIm][BF4] as electrolyte solvent. The potentiostatic electrolysis in ionic liquid afforded the desired product with a high yield. This result and the cyclic voltammetric investigation provide a better understanding of the reaction mechanism, which involves radical and iminium cation intermediates.

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

Some scientific research about 2-Phenyl-1,2,3,4-tetrahydroisoquinoline

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Visible-light photoredox catalysis in flow

Photoredox catalysis: A variety of organic transformations mediated by visible-light-active photoredox catalysts have been conducted in a photochemical flow reactor. The reactor design is very simple and can be easily implemented in any laboratory (see picture). In addition, this reactor afforded a marked increase in the reaction rate compared to those observed in typical batch (round bottom flask) reactors. Copyright

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

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Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow

Although carbon dioxide (CO 2) is highly abundant, its low reactivity has limited its use in chemical synthesis. In particular, methods for carbon-carbon bond formation generally rely on two-electron mechanisms for CO 2 activation and require highly activated reaction partners. Alternatively, radical pathways accessed via photoredox catalysis could provide new reactivity under milder conditions. Here we demonstrate the direct coupling of CO 2 and amines via the single-electron reduction of CO 2 for the photoredox-catalysed continuous flow synthesis of alpha-Amino acids. By leveraging the advantages of utilizing gases and photochemistry in flow, a commercially available organic photoredox catalyst effects the selective alpha-carboxylation of amines that bear various functional groups and heterocycles. The preliminary mechanistic studies support CO 2 activation and carbon-carbon bond formation via single-electron pathways, and we expect that this strategy will inspire new perspectives on using this feedstock chemical in organic synthesis.

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