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

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We herein report a versatile and environmentally friendly electrochemical oxidative C-H phosphonylation protocol. This protocol features a broad substrate scope; not only C(sp2)-H phosphonylation, but also C(sp3)-H phosphonylation is tolerated well under exogenous-oxidant-free and metal catalyst-free electrochemical oxidation conditions.

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

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Photoredox catalytic activation of organic molecules via single-electron transfer processes has proven to be a mild and efficient synthetic methodology. However, the heavy reliance on expensive ruthenium and iridium complexes limits their applications for scale-up synthesis. To this end, photoactive metal-organic frameworks (MOFs) exhibit unique advantages as novel heterogeneous photocatalytic systems, yet their utilization toward organic transformations has been limited. Here we describe the preparation and synthetic applications of four isostructural porphyrinic MOFs, namely, UNLPF-10a, -10b, -11, and -12, which are composed of free base, InIII-, SnIVCl2-, and SnIV-porphyrin building blocks, respectively. We demonstrate that the metalation with high valent metal cations (InIII and SnIV) significantly modifies the electronic structure of porphyrin macrocycle and provides a highly oxidative photoexcited state that can undergo efficient reductive quenching processes to facilitate organic reactions. In particular, UNLPF-12 exhibits both outstanding photostability and efficient photocatalytic activities toward a range of important organic transformations including aerobic hydroxylation of arylboronic acids, amine coupling, and the Mannich reaction.

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

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New Advances in Chemical Research in 2021. Chemistry is a science major with cience and engineering. The main research directions are chemical synthesis, and research on the structure and performance of functional materials.In a patent, 3340-78-1, name is 2-Phenyl-1,2,3,4-tetrahydroisoquinoline, introducing its new discovery. Synthetic Route of 3340-78-1

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

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Selective oxidation of amines using oxygen as terminal oxidant is an important area in green chemistry. In this work, we describe the use of graphite-supported gold nanoparticles (AuNPs/C) to catalyze aerobic oxidation of cyclic and acyclic benzylic amines to the corresponding imines with moderate-to-excellent substrate conversions (43-100%) and product yields (66-99%) (19 examples). Oxidation of N-substituted 1,2,3,4- tetrahydroisoquinolines in the presence of aqueous NaHCO3 solution gave the corresponding amides in good yields (83-93%) with high selectivity (up to amide/enamide=93:4) (6 examples). The same protocol can be applied to the synthesis of benzimidazoles from the reaction of o-phenylenediamines with benzaldehydes under aerobic conditions (8 examples). By simple centrifugation, AuNPs/C can be recovered and reused for ten consecutive runs for the oxidation of dibenzylamine to N-benzylidene(phenyl) methanamine without significant loss of catalytic activity and selectivity. This protocol “AuNPs/C+O 2” can be scaled to the gram scale, and 8.9 g (84% isolated yield) of 3,4-dihydroisoquinoline can be obtained from the oxidation of 10 g 1,2,3,4-tetrahydroisoquinoline in a onepot reaction. Based on the results of kinetic studies, radical traps experiment, and Hammett plot, a mechanism involving the hydrogen-transfer reaction from amine to metal and oxidation of M-H is proposed.

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

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

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An organocatalysis/copper-catalyzed asymmetric oxidative sp3 C-H olefination reaction of tertiary amines with olefins using molecular oxygen as the sole oxidant under mild conditions was realized for the first time. This novel strategy provides an efficient and environmentally friendly way to access diversify optically active C1-alkene tetrahydroisoquinoline derivatives.

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

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A Cu-catalyzed [4+1] annulation of N-aryl-1,2,3,4-tetrahydroisoquinolines (N-aryl THIQs) with alpha-diazoketones has been established under oxidative conditions, leading to the construction of a series of indolo[2,1-a]isoquinolines with generally good yields. The reaction enables dediazotized dicarbonylation of alpha-diazoketones, creating direct C(sp3)/C(sp2)?H bond bifunctionalization to access tetracyclic aza-heterocyclic skeletons.

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

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A third strategy for cross-dehydrogenative coupling reaction has been reported via platinum-catalyzed sp3 C-H and sp3 C-H coupling reaction in the absence of oxidant. Nitroalkanes as well as dialkyl malonate derivatives, beta-keto esters and malononitrile are active participants in this coupling reaction. Both cyclic and acyclic non-activated simple ketones are good reactants in this reaction.

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

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Isothioureas catalyze the enantioselective addition of 4-nitrophenyl esters to tetrahydroisoquinoline-derived iminium ions. 4-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the 4-nitrophenyl ester, is used to facilitate catalyst turnover in this reaction process. Optimization showed that 4-nitrophenyl esters give the best reactivity in this protocol over a range of alternative aryl esters, with the observed enantioselectivity markedly dependent on the nature of the iminium counterion. Highest yields and enantioselectivity were obtained using iminium bromide ions generated in situ via photoredox catalysis using BrCCl3 and Ru(bpy)3Cl2 (0.5 mol %) and commercially available tetramisole (5 mol %) as the Lewis base catalyst. The scope and limitations of this procedure was developed, giving the desired beta-amino amide products in up to 96% yield, 79:21 diastereomeric ratio (dr), and ermajor (2R,1?S) 99.5:0.5.

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