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

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Diethyl Phosphite Promoted Electrochemical Oxidation of Tetrahydroisoquinolines to 3,4-Dihydroisoquinolin-1(2 H)-ones

A diethyl phosphite mediated electrochemical oxidation strategy for the synthesis of 3,4-dihydroisoquinolin-1(2 H)-ones from tetrahydroisoquinolines under mild conditions has been developed. This protocol provides an environmentally friendly and simple way for the construction of C=O bonds in an undivided cell unit.

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

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Cationic Polycarbazole Networks as Visible-Light Heterogeneous Photocatalysts for Oxidative Organic Transformations

Photoredox catalysis has aroused great interest from chemists, as it offers a powerful tool for organic synthesis. Cationic polycarbazole networks (CPOP-28 and CPOP-29) were prepared via simple oxidative coupling reaction and applied as heterogeneous photocatalysts for a wide range of oxidative organic transformations, including oxidation of sulfides, hydroxylation of arylboronic acids, and cross-dehydrogenative coupling reactions, in the presence of visible light and air. Remarkably, photocatalytic activities are enhanced by ingenious introduction of trifluoromethyl groups to the polymeric network CPOP-29. The effects of the trifluoromethyl group on photocatalytic activities were elucidated in terms of photophysical and electrochemical properties. The appealing photocatalytic performance of the trifluoromethylated polymer is ascribed to superior light-absorption ability, longer fluorescence lifetime, and stronger oxidative capability. In addition, the photocatalysts showed good recyclability and could be reused after a simple separation workup.

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

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A convenient synthesis of deuterium labeled amines and nitrogen heterocycles with KOt-Bu/DMSO-d6

H/D exchanges of arylmethyl amines and nitrogen heterocycles were conveniently achieved with KOt-Bu/DMSO-d6. The method is also applicable for phenyl benzyl ethers, diarylmethanes, and alkyl arenes. These H/D exchange reactions are suggested to proceed via a free radical pathway.

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

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Iron-catalyzed oxidative mono- And bis-phosphonation of N,N-dialkylanilines

The dehydrogenative a-phosphonation of substituted N,N-dialkylanilines by dialkyl H-phosphonates was achieved under mild conditions by using environmentally benign iron(II) chloride as catalyst and teri-butyl hydroperoxide as oxidant. The reaction proceeded in the presence of electron-donating (methoxy, methyl, benzyl) and electron-withdrawing ring-substitutents (bromo, carbonyl, carboxyl, m-nitro) in moderate to good yields. The X-ray crystal structure of N-(5,5-dimethyl-2-oxo- 2lambda5-[1,3,2]dioxaphosphinan-2-yl-methyl)-N-methyl-p-toluidine was determined. Bis-(4-(dimethylamino)phe- nyl)methane and bis-4,4′- (dimethylamino)benzophenone underwent bisphosphonation selectively by respective monophosphonation at the remote dimethylamino groups. Furthermore, the use of excess dialkyl H-phosphonate and oxidant allowed us to functionalize both methyl groups of N(CH3)2 in N,N-dimethyl-p-toluidine and N,N-dimethylaminomesidine, respectively, to obtain alpha,alpha?- bisphosphonatoamines in high yield.

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

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The direct alpha-C(sp3)-H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing

An efficient nitro-Mannich type direct alpha-C(sp3)-H functionalisation of N-aryl-1,2,3,4-tetrahydroisoquinolines catalysed by simple iron salts in combination with O2 as the terminal oxidant is described. The use of a Teflon AF-2400 membrane Tube-in-Tube reactor under continuous flow conditions allowed for considerable process intensification to be achieved relative to previous batch methods. This journal is

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

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Synthesis of polycyclic amines through mild metal-free tandem cross-dehydrogenative coupling/intramolecular hydroarylation of N-aryltetrahydroisoquinolines and crotonaldehyde

A [4+2] cycloaddition reaction proceeding through tandem cross-dehydrogenative coupling/intramolecular hydroarylation between N-aryltetrahydroisoquinolines and crotonaldehyde was developed by virtue of enamine-iminium catalysis, which enabled the rapid construction of ring-fused tetrahydroquinolines. The first metal-free catalytic oxidative coupling of gamma-selective C(sp3)-H bonds of crotonaldehyde was realized by using a secondary amine catalyst and 2,3-dichloro-5,6-dicyanoquinone.

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

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Tracing and elucidating visible-light mediated oxidation and C-H functionalization of amines using mass spectrometry

The co-existing mechanism of visible light mediated direct oxidation and C-H functionalization of amines was investigated by capturing all the intermediates using online mass spectrometry. The two-step dehydrogenation of amine involving a proton coupled electron transfer (PCET) process was revealed for the first time.

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

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One-Pot-Three-Component Synthesis of 2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)oxazoles via DEAD-Promoted Oxidative Ugi/Wittig Reaction

A new efficient DEAD-promoted oxidative Ugi/Wittig reaction for the preparation of 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)oxazoles has been developed. The one-pot reactions of odorless isocyano(triphenylphosphoranylidene)acetates, carboxylic acids, and N-aryl-1,2,3,4-tetrahydroisoquinolines produced polysubstituted 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)oxazoles directly in good yields in the presence of DEAD oxidant.

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

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Reactivity and mechanistic insight into visible-light-induced aerobic cross-dehydrogenative coupling reaction by organophotocatalysts

With visible-light irradiation, a mild, simple, and efficient metal-free photocatalytic system for the facile construction of sp3-sp 3 C-C bonds between tertiary amines and activated C-H bonds has been achieved. Spectroscopic study and product analysis demonstrate for the first time that photoinduced electron transfer from N-aryl tetrahydroisoquinolines to eosin Y bis(tetrabutylammonium salt) (TBA-eosin Y) takes place to generate TBA-eosin Y radical anion, which can subsequently react with nucleophiles and molecular oxygen. More strikingly, electron spin resonance (ESR) measurements provide direct evidence for the formation of superoxide radical anions (O 2) rather than singlet oxygen (1O 2) during visible-light irradiation. This active species is therefore believed to be responsible for the large rate of acceleration of the aerobic photocatalytic reactions. Light work: With visible-light irradiation (lambda>450 nm), a mild, simple and efficient metal-free photocatalytic system for the facile construction of sp3-sp3 C-C bonds between tertiary amines and activated C-H bonds has been achieved (see scheme). Electron spin resonance measurements offer direct evidence for the formation of superoxide radical anions (O2) during visible-light irradiation. Copyright

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

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Dual catalysis: Combining photoredox and Lewis base catalysis for direct Mannich reactions

A dual catalytic system combining photoredox and Lewis base catalysis has been developed. By the appropriate choice of light source and catalyst, the photoredox cycle can be optimally modulated to match the base catalyzed reaction cycle to provide the corresponding products under mild reaction conditions.

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